Organic compound having cyano group and insecticides/miticides

ABSTRACT

The present invention is directed to compounds represented by Formula (1); 
                 
 
wherein A, R, X, Y and n are as defined in the description, the salts thereof, and insecticide/acaricide compositions characterized by comprising one or more of said compounds and/or said salts as the active ingredients.

FIELD OF INVENTION

The present invention relates to novel compounds and insecticidal/acaricidal compositions containing said compounds as active ingredients.

BACKGROUND ART

Until now, a large number of pest controlling agents, such as insecticides and acaricides, have been used. However, many of them are scarcely satisfactory as pest controlling agents for a number of reasons: insufficient efficacy, restrictions on their use due to pesticide resistance problems, phytotoxicity or pollution on plants, or strong toxicity on humans, domestic animals and fishes. Therefore, there has been a desire for the development of pest controlling agents that are applicable safely and have fewer of the above-mentioned drawbacks.

Acrylonitrile derivatives similar to the compounds of the present invention are disclosed in EP 189960, WO97/40009, WO98/42683, WO98/35935, WO99/44993, etc.

Further, WO98/35935 has disclosed compounds represented by the following chemical structure that is shown in the Table I-d thereof. However, there is no description in this reference on their insecticidal and/or acaricidal activities.

DISCLOSURE OF THE INVENTION

It is an object of the present invention to provide novel compounds which can be used as the active ingredients of insecticides and acaricides capable of being easily manufactured in an industrial scale, providing firm efficacy, and being applicable safely.

The present invention is directed to compounds represented by Formula (1) and insecticidal/acaricidal compositions characterized by comprising one or more of the compounds represented by said Formula (1) as the active ingredient(s).

In the above Formula (1);

A is phenyl substituted by W or a heterocyclic group substituted by W;

wherein W is nitro, cyano, halogeno, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, phenyl optionally substituted by G₁, or phenoxy optionally substituted by G₁;

wherein G₁ is nitro, cyano, halogeno, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl, or C₁₋₆ alkoxycarbonyl;

said heterocyclic group is a 5- or 6-membered heterocyclic group that contains at least one heteroatom selected from a group consisting of oxygen, sulfur and nitrogen;

when either of said phenyl or said heterocyclic group contains 2 or more substituents W, W may be the same or different from each other;

R is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy C₁₋₆ alkyl, C₁₋₆ alkylcarbonyloxy C₁₋₆ alkyl, C₃₋₆ cycloalkylcarbonyloxy C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyloxy C₁₋₆ alkyl, optionally substituted phenylcarbonyloxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, C₁₋₆ alkylcarbonylthio C₁₋₆ alkyl, C₃₋₆ cycloalkylcarbonylthio C₁₋₆ alkyl, C₁₋₆ alkoxycarbonylthio C₁₋₆ alkyl, optionally substituted phenylcarbonylthio C₁₋₆ alkyl, optionally substituted phenyl C₁₋₆ alkyl, a group represented by a formula of COR₁, a group represented by a formula of CSR₁, or a group represented by a formula of SO₂R₂;

wherein R₁ is C₁₋₁₂ alkyl, C₃₋₆ cycloalkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, optionally substituted phenyl C₁₋₆ alkyl, optionally substituted phenyl C₁₋₆ alkoxy, or optionally substituted phenyl, and

R₂ is C₁₋₁₂ alkyl or optionally substituted phenyl;

X is nitro, cyano, halogeno, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₁₋₆ haloalkyl, C₂₋₆ haloalkenyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₂₋₆ alkenyloxy, C₂₋₆ haloalkenyloxy, C₂₋₆ alkynyloxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, tri-C₁₋₆ alkylsilyl, C₁₋₆ alkoxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, C₁₋₆ alkylsulfinyl C₁₋₆ alkyl, C₁₋₆ alkylsulfonyl C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, phenyl C₁₋₆ alkyl optionally substituted by G₂, phenyl C₁₋₆ alkoxy optionally substituted by G₂, thienyl optionally substituted by G₃, pyridyl optionally substituted by G₂, pyridyloxy optionally substituted by G₂, phenyl optionally substituted by G₄, or phenoxy optionally substituted by G₄;

wherein G₂ is C₁₋₆ alkyl, halogeno, C₁₋₆ haloalkyl, or C₁₋₆ haloalkoxy,

G₃ is C₁₋₆ alkyl or halogeno, and

G₄ is nitro, cyano, halogeno, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl, or C₁₋₆ alkoxycarbonyl;

n is 0, or an integer of 1 to 5, and when n is 2 or more, the above X may be same or different from each other; and

Y is oxygen, sulfur, or nitrogen substituted by either hydrogen or C₁₋₆ alkyl.

MODE FOR CARRYING OUT THE INVENTION

In the above Formula (1),

A is phenyl substituted by W, or a heterocyclic group substituted by W;

W is nitro, cyano,

halogeno, such as fluoro, chloro, bromo and iodo,

C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C₃₋₆ cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoromethyl, and pentafluoroethyl,

C₁₋₆ alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and t-butoxy,

C₁₋₆ haloalkoxy, such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, and 1,1-difluoroethoxy,

C₁₋₆ alkylthio, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio,

C₁₋₆ alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, and butylsulfinyl,

C₁₋₆ alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, and n-butylsulfonyl,

C₁₋₆ alkylamino, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, and n-pentylamino,

di-C₁₋₆ alkylamino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, and methylpropylamino,

C₁₋₆ alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, and n-butylcarbonyl,

C₁₋₆ alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl,

phenyl optionally substituted by G₁, or phenoxy optionally substituted by G₁;

wherein G₁ is nitro, cyano,

halogeno, such as fluoro, chloro, bromo and iodo,

C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and t-butyl,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl,

C₁₋₆ alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and t-butoxy,

C₁₋₆ haloalkoxy, such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, and 1,1-difluoroethoxy,

C₁₋₆ alkylthio, such as methylthio, ethylthioethyl, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio,

C₁₋₆ alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, and butylsulfinyl,

C₁₋₆ alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, and butylsulfonyl,

C₁₋₆ alkylamino, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, and n-pentylamino,

di-C₁₋₆ alkylamino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, methylpropylamino, and methylbutylamino,

C₁₋₆ alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, propylcarbonyl and butylcarbonyl, or

C₁₋₆ alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl.

In the above Formula (1), said heterocyclic group optionally substituted by W is a 5- or 6-membered heterocyclic group containing 1 to 4 atoms of nitrogen, oxygen or sulfur, which is, for example, triazolyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, or the like. More specifically, the examples of said heterocyclic group optionally substituted by W include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, 1,2,4-triazol-3-yl, 1,2,3-triazol-4-yl, tetrazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazole-5-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 5-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl, and the like.

Note that, when said phenyl or said heterocyclic group contains 2 or more substituents W, W may be the same or different from each other.

In the above Formula (1),

R is hydrogen,

C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl and isomers thereof, and hexyl and isomers thereof,

C₁₋₆ alkoxy C₁₋₆ alkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl, and butoxymethyl,

C₁₋₆ alkylcarbonyloxy C₁₋₆ alkyl, such as acetoxymethyl, pivaloyloxymethyl, heptanoyloxymethyl, acetoxyethyl, and acetoxyhexyl,

C₃₋₆ cycloalkylcarbonyloxy C₁₋₆ alkyl, such as cyclopropylcarbonyloxymethyl, cyclopentylcarbonyloxymethyl, cyclohexylcarbonyloxymethyl, cyclopropylcarbonyloxyethyl, and cyclopropylcarbonyloxyhexane,

C₁₋₆ alkoxycarbonyloxy C₁₋₆ alkyl, such as methoxycarbonyloxymethyl, 1-(methoxycarbonyloxy)ethyl, ethoxycarbonyloxymethyl, propoxycarbonyloxymethyl, isopropoxycarbonyloxymethyl, butoxycarbonyloxymethyl, and t-butoxycarbonyloxymethyl,

phenylcarbonyloxy C₁₋₆ alkyl, such as optionally substituted benzoyloxymethyl and 1-(benzoyloxy)ethyl,

C₁₋₆ alkylthio C₁₋₆ alkyl, such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl, and butylthiomethyl,

C₁₋₆ alkylcarbonylthio C₁₋₆ alkyl, such as methylcarbonylthiomethyl, methylcarbonylthioethyl, 1-(methylcarbonylthio)ethyl, ethylcarbonylthiomethyl, propylcarbonylthiomethyl, and butylcarbonylthiomethyl,

C₃₋₆ cycloalkylcarbonylthio C₁₋₆ alkyl, such as cyclopropylcarbonylthiomethyl, cyclopropylcarbonylthioethyl, 1-(cyclopropylcarbonylthio)ethyl, cyclobutylcarbonylthiomethyl, cyclopentylcarbonylthiomethyl, and cyclohexylcarbonylthiomethyl,

C₁₋₆ alkoxycarbonylthio C₁₋₆ alkyl, such as methoxycarbonylthiomethyl, 1-methoxycarbonylthioethyl, ethoxycarbonylthiomethyl, propoxycarbonylthiomethyl, isopropoxycarbonylthiomethyl, butoxycarbonylthiomethyl, and t-butoxycarbonylthiomethyl,

phenylcarbonylthio C₁₋₆ alkyl, such as optionally substituted benzoylthiomethyl, and benzoylthioethyl,

phenyl C₁₋₆ alkyl, such as optionally substituted benzyl and phenetyl,

a group represented by a formula of COR₁, a group represented by a formula of CSR₁, or a group represented by a formula of SO₂R₂;

wherein R₁ is C₁₋₁₂ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-nonyl and isomers thereof, and dodecyl,

C₃₋₆ cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl,

C₁₋₆ alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, and t-butoxy,

C₁₋₆ alkylthio, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio,

C₁₋₆ alkylamino, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, and n-pentylamino,

di-C₁₋₆ alkylamino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, methylpropylamino, and methylbutylamino,

optionally substituted phenyl C₁₋₆ alkyl,

optionally substituted phenyl C₁₋₆ alkoxy, or

optionally substituted phenyl; and

R₂ is C₁₋₁₂ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-nonyl and isomers thereof, and n-dodecyl, or optionally substituted phenyl,

said substituent for substituting said phenyl respectively contained in said R, R₁ and R₂ is, for example, halogeno, such as fluoro, chloro, bromo and iodo, C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and t-butyl, C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, and trichloroethyl, or C₁₋₆ alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy;

said phenyl C₁₋₆ alkyl of said optionally substituted phenyl C₁₋₆ alkyl exampled for said R₁ is, for example, benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenyl-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, and the like, and said phenyl C₁₋₆ alkoxy of said optionally substituted phenyl C₁₋₆ alkoxy exampled for said R₁ is, for example, benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenyl-1-methylethoxy, 1-phenylpropoxy, 2-phenylpropoxy, 3-phenylpropoxy and the like;

X is nitro, cyano,

halogeno, such as fluoro, chloro, bromo, and iodo,

C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C₂₋₆ alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl,

C₂₋₆ alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, and 1,1-dimethyl-2-butynyl,

C₃₋₈ cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl,

C₂₋₆ haloalkenyl, such as 3-chloro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-difluoro-3-butenyl, and 3,3,-dichloro-2-propenyl,

C₁₋₆ alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and t-butoxy,

C₁₋₆ haloalkoxy, such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, 2,2,2-trifluoroethoxy, and pentafluoroethoxy,

C₂₋₆ alkenyloxy, such as allyloxy, 2-propenyloxy, 2-butenyloxy, and 2-methyl-3-propenyloxy,

C₂₋₆ haloalkenyloxy, such as 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy, and 4,4-difluoro-3-butenyloxy,

C₂₋₆ alkynyloxy, such as 2-propynyloxy, 2-butynyloxy, and 1-methyl-2-propynyloxy,

C₁₋₆ alkylthio, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio,

C₁₋₆ alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, and butylsulfinyl,

C₁₋₆ alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, and butylsulfonyl,

C₁₋₆ alkylamino, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, and n-pentylamino,

di-C₁₋₆ alkylamino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, and methylpropylamino,

C₁₋₆ alkylsilyl such as trimethylsilyl,

C₁₋₆ alkoxy C₁₋₆ alkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl, and butoxymethyl,

C₁₋₆ alkylthio C₁₋₆ alkyl, such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl, and butylthiomethyl,

C₁₋₆ alkylsulfinyl C₁₋₆ alkyl, such as methylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylethyl, ethylsulfinylmethyl, propylsulfinylmethyl, and butylsulfinylmethyl,

C₁₋₆ alkylsulfonyl C₁₋₆ alkyl, such as methylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl, ethylsulfonylmethyl, propylsulfonylmethyl, and butylsulfonylmethyl,

C₁₋₆ alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, and butylcarbonyl,

C₁₋₆ alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, and t-butoxycarbonyl,

phenyl C₁₋₆ alkyl optionally substituted by G₂,

phenyl C₁₋₆ alkoxy optionally substituted by G₂,

optionally substituted thienyl by G₃, optionally substituted pyridyl by G₂,

pyridyloxy optionally substituted by G₂, phenyl optionally substituted by G4, or phenoxy optionally substituted by G₄;

wherein G₂ is C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

halogeno, such as fluoro, chloro, bromo, and iodo,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl, or

C₁₋₆ haloalkoxy, such as chloromethoxy, fluoromethoxy, bromomethoxy, dichloromethoxy, difluoromethoxy, dibromomethoxy, trichloromethoxy, trifluoromethoxy, tribromomethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, and perfluoropropoxy,

G₃ is C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof, or

halogeno, such as fluoro, chloro, bromo, and iodo,

G₄ is nitro, cyano,

C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C₁₋₆ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, and pentafluoroethyl,

C₁₋₆ alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and t-butoxy,

C₁₋₆ haloalkoxy, such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, and 1,1-difluoroethoxy,

C₁₋₆ alkylthio, such as methylthio, ethylthioethyl, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio,

C₁₋₆ alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, and n-butylsulfinyl,

C₁₋₆ alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, and n-butylsulfonyl,

C₁₋₆ alkylamino, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, and n-pentylamino,

di-C₁₋₆ alkylamino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, and methylpropylamino,

C₁₋₆ alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, and n-butylcarbonyl, or

C₁₋₆ alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl;

n is 0 or an integer of 1 to 5, and when n is 2 or more, X may be same or different from each other, and

Y is oxygen, sulfur, or nitrogen substituted by either hydrogen or C₁₋₆ alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl.

The compounds of the present invention can be prerared, for example, according to the following process. Process for preparing a compound represented by the Formula (1) wherein R is hydrogen:

In the above reaction formula, A, X, Y and n are as defined above, and L₁ is halogeno, C₁₋₆ alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, methanesulfonyloxy, or an eliminating group, such as trifluoromethanesulfonyl.

A compound represented by the above Formula (2) is obtainable by causing a compound represented by the above Formula (3) to react with a compound represented by the above Formula (4) in the presence of a base. Examples of the base to be used in this reaction include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, n-butyl lithium, lithium diisopropylamide (LDA), sodium hydride, potassium hydride, triethylamine, diisopropylamine, pyridine, etc. Further, N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), tetrahydrofuran (THF), acetonitrile, hexamethylphosphoric triamide (HMPT), benzene, toluene, dichloromethane, chloroform, carbon tetrachloride and the like may be used as the solvent to be used in the above reaction. The reaction temperature for the above reaction is preferably set at a temperature in a range of from −78° C. to the boiling point of the solvent used.

Note that the compounds represented by the above Formula (2) exist in tautomers of two forms, that is, the keto-form (2′) and the enol-form (2), and all of these tautomers fall within the scope of the compounds of the present invention.

Process for producing a compound represented by the Formula (1) wherein R is a group other than hydrogen:

In the above reaction formula, A, R₁, X, Y and n are as defined above, R′ is as defined above for R except hydrogen, and L₂ is halogeno, C₁₋₆ alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, methanesulfonyloxy, or an eliminating group such as trifluoromethanesulfonyloxy.

A compound represented by the above Formula (1′) is obtainable by causing a compound represented by the above Formula (2) to react with a compound represented by the above Formula (5) or (6) in the presence of a base.

Examples of said base used for this reaction include alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide, carbonates, such as sodium carbonate and potassium carbonate, organic metals, such as n-butyl lithium, LDA, metal hydrides, such as sodium hydride and potassium hydride, and organic bases, such as triethylamine, diisopropylamine and pyridine.

Further, solvents able to be used in the above reaction include DMF, DMSO, THF, acetonitrile, HMPT, benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, and the like. Preferred reaction temperature are from −78° C. to the boiling point of solvent used.

Note that there are stereoisomers having the structural formula represented by Formula (1″) in the compounds represented by the Formula (1) of the present invention. Depending on the reaction conditions and the purification process, either one of the isomers may be obtained, or the mixture of the isomers may be obtained, and it should be noted that all of these isomers fall within the scope of the compounds of the present invention.

A target compound is obtained with usual post-treatments after the completion of the reaction.

The structures of the compounds of the present invention were determined by IR, MNR, MS and other means.

Representative examples of the compounds of the present invention, that can be prepared according to the above processes, are shown in Tables 1 and 2.

Note that the symbols used in the tables have the following meanings: Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Pen: pentyl, Hex: hexyl, Ph: phenyl, n: normal, i: iso, t: tertiary, c: cyclo

TABLE 1

1-1 1-2 1-3 1-4

1-5 1-6 1-7 1-8 Combinations of A, R and Xn of all compounds represented in the above formula 1-1 through 1-8 are exemplified in the following tables. A R Xn A R Xn A R Xn a1 r6 — a26 r6 4-CN a7 r6 4-F a2 r6 — a35 r6 4-CN a8 r6 4-F a4 r6 — a1 r1 4-F a9 r6 4-F a23 r6 — a1 r6 4-F a10 r6 4-F a25 r6 — a1 r22 4-F a11 r6 4-F a26 r6 — a1 r43 4-F a12 r6 4-F a35 r6 — a1 r52 4-F a13 r6 4-F a1 r6 4-NO₂ a2 r1 4-F a14 r6 4-F a2 r6 4-NO₂ a2 r6 4-F a15 r6 4-F a4 r6 4-NO₂ a2 r22 4-F a16 r6 4-F a23 r6 4-NO₂ a2 r43 4-F a17 r6 4-F a25 r6 4-NO₂ a2 r52 4-F a18 r6 4-F a26 r6 4-NO₂ a3 r6 4-F a19 r6 4-F a35 r6 4-NO₂ a3 r22 4-F a20 r6 4-F a1 r6 4-CN a4 r6 4-F a21 r6 4-F a2 r6 4-CN a4 r22 4-F a22 r6 4-F a4 r6 4-CN a5 r6 4-F a23 r1 4-F a23 r6 4-CN a5 r22 4-F a23 r6 4-F a25 r6 4-CN a6 r6 4-F a23 r22 4-F a23 r43 4-F a25 r25 4-F a25 r56 4-F a23 r52 4-F a25 r26 4-F a25 r57 4-F a24 r1 4-F a25 r27 4-F a25 r58 4-F a24 r6 4-F a25 r28 4-F a25 r59 4-F a24 r22 4-F a25 r29 4-F a25 r60 4-F a24 r43 4-F a25 r30 4-F a25 r61 4-F a24 r52 4-F a25 r31 4-F a25 r62 4-F a25 r1 4-F a25 r32 4-F a25 r63 4-F a25 r2 4-F a25 r33 4-F a25 r64 4-F a25 r3 4-F a25 r34 4-F a25 r65 4-F a25 r4 4-F a25 r35 4-F a25 r66 4-F a25 r5 4-F a25 r36 4-F a25 r67 4-F a25 r6 4-F a25 r37 4-F a25 CH₂OEt 4-F a25 r7 4-F a25 r38 4-F a25 CH₂SEt 4-F a25 r8 4-F a25 r39 4-F a25 CH₂Ph 4-F a25 r9 4-F a25 r40 4-F a25 Me 4-F a25 r10 4-F a25 r41 4-F a25 nHex 4-F a25 r11 4-F a25 r42 4-F a26 r1 4-F a25 r12 4-F a25 r43 4-F a26 r6 4-F a25 r13 4-F a25 r44 4-F a26 r22 4-F a25 r14 4-F a25 r45 4-F a26 r43 4-F a25 r15 4-F a25 r46 4-F a26 r52 4-F a25 r16 4-F a25 r47 4-F a27 r1 4-F a25 r17 4-F a25 r48 4-F a27 r6 4-F a25 r18 4-F a25 r49 4-F a27 r22 4-F a25 r19 4-F a25 r50 4-F a27 r43 4-F a25 r20 4-F a25 r51 4-F a27 r52 4-F a25 r21 4-F a25 r52 4-F a28 r1 4-F a25 r22 4-F a25 r53 4-F a28 r6 4-F a25 r23 4-F a25 r54 4-F a28 r22 4-F a25 r24 4-F a25 r55 4-F a28 r43 4-F a28 r52 4-F a35 r6 4-F a44 r6 4-F a29 r1 4-F a35 r22 4-F a45 r6 4-F a29 r6 4-F a35 r43 4-F a46 r6 4-F a29 r22 4-F a35 r52 4-F a47 r6 4-F a29 r43 4-F a36 r1 4-F a48 r6 4-F a29 r52 4-F a36 r6 4-F a49 r6 4-F a30 r1 4-F a36 r22 4-F a50 r6 4-F a30 r6 4-F a36 r43 4-F a51 r6 4-F a30 r22 4-F a36 r52 4-F a52 r6 4-F a30 r43 4-F a37 r6 4-F a53 r6 4-F a30 r52 4-F a38 r1 4-F a54 r6 4-F a31 r1 4-F a38 r6 4-F a55 r6 4-F a31 r6 4-F a38 r22 4-F a56 r6 4-F a31 r22 4-F a38 r43 4-F a57 r6 4-F a31 r43 4-F a38 r52 4-F a58 r6 4-F a31 r52 4-F a39 r1 4-F a59 r6 4-F a32 r1 4-F a39 r6 4-F a1 r1 4-Cl a32 r6 4-F a39 r22 4-F a1 r6 4-Cl a32 r22 4-F a39 r43 4-F a1 22 4-Cl a32 r43 4-F a39 r52 4-F a1 r43 4-Cl a32 r52 4-F a40 r1 4-F a1 r52 4-Cl a33 r1 4-F a40 r6 4-F a2 r1 4-Cl a33 r6 4-F a40 r22 4-F a2 r6 4-Cl a33 r22 4-F a40 r43 4-F a2 r22 4-Cl a33 r43 4-F a40 r52 4-F a2 r43 4-Cl a33 r52 4-F a41 r1 4-F a2 r52 4-Cl a34 r1 4-F a41 r6 4-F a3 r6 4-Cl a34 r6 4-F a41 r22 4-F a3 r22 4-Cl a34 r22 4-F a41 r43 4-F a4 r6 4-Cl a34 r43 4-F a41 r52 4-F a4 r22 4-Cl a34 r52 4-F a42 r6 4-F a5 r6 4-Cl a35 r1 4-F a43 r6 4-F a5 r22 4-Cl a6 r6 4-Cl a25 r5 4-Cl a25 r36 4-Cl a7 r6 4-Cl a25 r6 4-Cl a25 r37 4-Cl a8 r6 4-Cl a25 r7 4-Cl a25 r38 4-Cl a9 r6 4-Cl a25 r8 4-Cl a25 r39 4-Cl a10 r6 4-Cl a25 r9 4-Cl a25 r40 4-Cl a11 r6 4-Cl a25 r10 4-Cl a25 r41 4-Cl a12 r6 4-Cl a25 r1 4-Cl a25 r42 4-Cl a13 r6 4-Cl a25 r12 4-Cl a25 r43 4-Cl a14 r6 4-Cl a25 r13 4-Cl a25 r44 4-Cl a15 r6 4-Cl a25 r14 4-Cl a25 r45 4-Cl a16 r6 4-Cl a25 r15 4-Cl a25 r46 4-Cl a17 r6 4-Cl a25 r16 4-Cl a25 r47 4-Cl a18 r6 4-Cl a25 r17 4-Cl a25 r48 4-Cl a19 r6 4-Cl a25 r18 4-Cl a25 r49 4-Cl a20 r6 4-Cl a25 r19 4-Cl a25 r50 4-Cl a21 r6 4-Cl a25 r20 4-Cl a25 r51 4-Cl a22 r6 4-Cl a25 r21 4-Cl a25 r52 4-Cl a23 r1 4-Cl a25 r22 4-Cl a25 r53 4-Cl a23 r6 4-Cl a25 r23 4-Cl a25 r54 4-Cl a23 r22 4-Cl a25 r24 4-Cl a25 r55 4-Cl a23 r43 4-Cl a25 r25 4-Cl a25 r56 4-Cl a23 r52 4-Cl a25 r26 4-Cl a26 r57 4-Cl a24 r1 4-Cl a25 r27 4-Cl a25 r58 4-Cl a24 r6 4-Cl a25 r28 4-Cl a25 r59 4-Cl a24 r22 4-Cl a25 r29 4-Cl a25 r60 4-Cl a24 r43 4-Cl a25 r30 4-Cl a25 r61 4-Cl a24 r52 4-Cl a25 r31 4-Cl a25 r62 4-Cl a25 r1 4-Cl a25 r32 4-Cl a25 r63 4-Cl a25 r2 4-Cl a25 r33 4-Cl a25 r64 4-Cl a25 r3 4-Cl a25 r34 4-Cl a25 r65 4-Cl a25 r4 4-Cl a25 r35 4-Cl a26 r66 4-Cl a25 r67 4-Cl a31 r6 4-Cl a38 r22 4-Cl a25 CH₂OEt 4-Cl a31 r22 4-Cl a38 r43 4-Cl a25 CH₂SEt 4-Cl a31 r43 4-Cl a38 r52 4-Cl a25 CH₂Ph 4-Cl a31 r52 4-Cl a39 r1 4-Cl a25 Me 4-Cl a32 r1 4-Cl a39 r6 4-Cl a25 nHex 4-Cl a32 r6 4-Cl a39 r22 4-Cl a26 r1 4-Cl a32 r22 4-Cl a39 r43 4-Cl a26 r6 4-Cl a32 r43 4-Cl a39 r52 4-Cl a26 r22 4-Cl a32 r52 4-Cl a40 r1 4-Cl a26 r43 4-Cl a33 r1 4-Cl a40 r6 4-Cl a26 r52 4-Cl a33 r6 4-Cl a40 r22 4-Cl a27 r1 4-Cl a33 r22 4-Cl a40 r43 4-Cl a27 r6 4-Cl a33 r43 4-Cl a40 r52 4-Cl a27 r22 4-Cl a33 r52 4-Cl a41 r1 4-Cl a27 r43 4-Cl a34 r1 4-Cl a41 r6 4-Cl a27 r52 4-Cl a34 r6 4-Cl a41 r22 4-Cl a28 r1 4-Cl a34 r22 4-Cl a41 r43 4-Cl a28 r6 4-Cl a34 r43 4-Cl a41 r52 4-Cl a28 r22 4-Cl a34 r52 4-Cl a42 r6 4-Cl a28 r43 4-Cl a35 r1 4-Cl a43 r6 4-Cl a28 r52 4-Cl a35 r6 4-Cl a44 r6 4-Cl a29 r1 4-Cl a35 r22 4-Cl a45 r6 4-Cl a29 r6 4-Cl a35 r43 4-Cl a46 r6 4-Cl a29 r22 4-Cl a35 r52 4-Cl a47 r6 4-Cl a29 r43 4-Cl a36 r1 4-Cl a48 r6 4-Cl a29 r52 4-Cl a36 r6 4-Cl a49 r6 4-Cl a30 r1 4-Cl a36 r22 4-Cl a50 r6 4-Cl a30 r6 4-Cl a36 r43 4-Cl a51 r6 4-Cl a30 r22 4-Cl a36 r52 4-Cl a52 r6 4-Cl a30 r43 4-Cl a37 r6 4-Cl a53 r6 4-Cl a30 r52 4-Cl a38 r1 4-Cl a54 r6 4-Cl a31 r1 4-Cl a38 r6 4-Cl a55 r6 4-Cl a56 r6 4-Cl a35 r6 4-iPr a1 r22 4-CF₃ a57 r6 4-Cl a1 r6 4-tBu a1 r43 4-CF₃ a58 r6 4-Cl a2 r6 4-tBu a1 r52 4-CF₃ a59 r6 4-Cl a4 r6 4-tBu a2 r1 4-CF₃ a1 r6 4-Br a23 r6 4-tBu a2 r6 4-CF₃ a2 r6 4-Br a25 r6 4-tBu a2 r22 4-CF₃ a4 r6 4-Br a26 r6 4-tBu a2 r43 4-CF₃ a23 r6 4-Br a35 r6 4-tBu a2 r52 4-CF₃ a25 r6 4-Br a1 r6 4-nHex a3 r6 4-CF₃ a26 r6 4-Br a2 r6 4-nHex a3 r22 4-CF₃ a35 r6 4-Br a4 r6 4-nHex a4 r6 4-CF₃ a1 r6 4-I a23 r6 4-nHex a4 r22 4-CF₃ a2 r6 4-I a25 r6 4-nHex a5 r6 4-CF₃ a4 r6 4-I a26 r6 4-nHex a5 r22 4-CF₃ a23 r6 4-I a35 r6 4-nHex a6 r6 4-CF₃ a25 r6 4-I a1 r6 4-cPr a7 r6 4-CF₃ a26 r6 4-I a2 r6 4-cPr a8 r6 4-CF₃ a35 r6 4-I a4 r6 4-cPr a9 r6 4-CF₃ a1 r6 4-Me a23 r6 4-cPr a10 r6 4-CF₃ a2 r6 4-Me a25 r6 4-cPr a11 r6 4-CF₃ a4 r6 4-Me a26 r6 4-cPr a12 r6 4-CF₃ a23 r6 4-Me a35 r6 4-cPr a13 r6 4-CF₃ a25 r6 4-Me a1 r6 4-cHex a14 r6 4-CF₃ a26 r6 4-Me a2 r6 4-cHex a15 r6 4-CF₃ a35 r6 4-Me a4 r6 4-cHex a16 r6 4-CF₃ a1 r6 4-iPr a23 r6 4-cHex a17 r6 4-CF₃ a2 r6 4-iPr a25 r6 4-cHex a18 r6 4-CF₃ a4 r6 4-iPr a26 r6 4-cHex a19 r6 4-CF₃ a23 r6 4-iPr a35 r6 4-cHex a20 r6 4-CF₃ a25 r6 4-iPr a1 r1 4-CF₃ a21 r6 4-CF₃ a26 r6 4-iPr a1 r6 4-CF₃ a22 r6 4-CF₃ a23 r1 4-CF₃ a25 r22 4-CF₃ a25 r53 4-CF₃ a23 r6 4-CF₃ a25 r23 4-CF₃ a25 r54 4-CF₃ a23 r22 4-CF₃ a25 r24 4-CF₃ a25 r55 4-CF₃ a23 r43 4-CF₃ a25 r25 4-CF₃ a25 r56 4-CF₃ a23 r52 4-CF₃ a25 r26 4-CF₃ a25 r57 4-CF₃ a24 r1 4-CF₃ a25 r27 4-CF₃ a25 r58 4-CF₃ a24 r6 4-CF₃ a25 r28 4-CF₃ a25 r59 4-CF₃ a24 r22 4-CF₃ a25 r29 4-CF₃ a25 r60 4-CF₃ a24 r43 4-CF₃ a25 r30 4-CF₃ a25 r61 4-CF₃ a24 r52 4-CF₃ a25 r31 4-CF₃ a25 r62 4-CF₃ a25 r1 4-CF₃ a25 r32 4-CF₃ a25 r63 4-CF₃ a25 r2 4-CF₃ a25 r33 4-CF₃ a25 r64 4-CF₃ a25 r3 4-CF₃ a25 r34 4-CF₃ a25 r65 4-CF₃ a25 r4 4-CF₃ a25 r35 4-CF₃ a25 r66 4-CF₃ a25 r5 4-CF₃ a25 r36 4-CF₃ a25 r67 4-CF₃ a25 r6 4-CF₃ a25 r37 4-CF₃ a25 CH₂OEt 4-CF₃ a25 r7 4-CF₃ a25 r38 4-CF₃ a25 CH₂SEt 4-CF₃ a25 r8 4-CF₃ a25 r39 4-CF₃ a25 CH₂Ph 4-CF₃ a25 r9 4-CF₃ a25 r40 4-CF₃ a25 Me 4-CF₃ a25 r10 4-CF₃ a25 r41 4-CF₃ a25 nHex 4-CF₃ a25 r1 4-CF₃ a25 r42 4-CF₃ a26 r1 4-CF₃ a25 n12 4-CF₃ a25 r43 4-CF₃ a26 r6 4-CF₃ a25 n13 4-CF₃ a25 r44 4-CF₃ a26 r22 4-CF₃ a25 n14 4-CF₃ a25 r45 4-CF₃ a26 r43 4-CF₃ a25 n15 4-CF₃ a25 r46 4-CF₃ a26 r52 4-CF₃ a25 r16 4-CF₃ a25 r47 4-CF₃ a27 r1 4-CF₃ a25 n17 4-CF₃ a25 r48 4-CF₃ a27 r6 4-CF₃ a25 n18 4-CF₃ a25 r49 4-CF₃ a27 r22 4-CF₃ a25 n19 4-CF₃ a25 r50 4-CF₃ a27 r43 4-CF₃ a25 r20 4-CF₃ a25 r51 4-CF₃ a27 r52 4-CF₃ a25 r21 4-CF₃ a25 r52 4-CF₃ a28 r1 4-CF₃ a28 r6 4-CF₃ a34 r43 4-CF₃ a41 r52 4-CF₃ a28 r22 4-CF₃ a34 r52 4-CF₃ a42 r6 4-CF₃ a28 r43 4-CF₃ a35 r1 4-CF₃ a43 r6 4-CF₃ a28 r52 4-CF₃ a35 r6 4-CF₃ a44 r6 4-CF₃ a29 r1 4-CF₃ a35 r22 4-CF₃ a45 r6 4-CF₃ a29 r6 4-CF₃ a35 r43 4-CF₃ a46 r6 4-CF₃ a29 r22 4-CF₃ a35 r52 4-CF₃ a47 r6 4-CF₃ a29 r43 4-CF₃ a36 r1 4-CF₃ a48 r6 4-CF₃ a29 r52 4-CF₃ a36 r6 4-CF₃ a49 r6 4-CF₃ a30 r1 4-CF₃ a36 r22 4-CF₃ a50 r6 4-CF₃ a30 r6 4-CF₃ a36 r43 4-CF₃ a51 r6 4-CF₃ a30 r22 4-CF₃ a36 r52 4-CF₃ a52 r6 4-CF₃ a30 r43 4-CF₃ a37 r6 4-CF₃ a53 r6 4-CF₃ a30 r52 4-CF₃ a38 r1 4-CF₃ a54 r6 4-CF₃ a31 r1 4-CF₃ a38 r6 4-CF₃ a55 r6 4-CF₃ a31 r6 4-CF₃ a38 r22 4-CF₃ a56 r6 4-CF₃ a31 r22 4-CF₃ a38 r43 4-CF₃ a57 r6 4-CF₃ a31 r43 4-CF₃ a38 r52 4-CF₃ a58 r6 4-CF₃ a31 r52 4-CF₃ a39 r1 4-CF₃ a59 r6 4-CF₃ a32 r1 4-CF₃ a39 r6 4-CF₃ a1 r6 4-OMe a32 r6 4-CF₃ a39 r22 4-CF₃ a2 r6 4-OMe a32 r22 4-CF₃ a39 r43 4-CF₃ a4 r6 4-OMe a32 r43 4-CF₃ a39 r52 4-CF₃ a23 r6 4-OMe a32 r52 4-CF₃ a40 r1 4-CF₃ a25 r6 4-OMe a33 r1 4-CF₃ a40 r6 4-CF₃ a26 r6 4-OMe a33 r6 4-CF₃ a40 r22 4-CF₃ a35 r6 4-OMe a33 r22 4-CF₃ a40 r43 4-CF₃ a1 r6 4-OiPr a33 r43 4-CF₃ a40 r52 4-CF₃ a2 r6 4-OiPr a33 r52 4-CF₃ a41 r1 4-CF₃ a4 r6 4-OiPr a34 r1 4-CF₃ a41 r6 4-CF₃ a23 r6 4-OiPr a34 r6 4-CF₃ a41 r22 4-CF₃ a25 r6 4-OiPr a34 r22 4-CF₃ a41 r43 4-CF₃ a26 r6 4-OiPr a35 r6 4-OiPr a25 r6 4-COMe a2 r6 2-Cl a1 r6 4-OtBu a35 r6 4-COMe a4 r6 2-Cl a2 r6 4-OtBu a25 r6 4-COtBu a23 r6 2-Cl a4 r6 4-OtBu a35 r6 4-COtBu a25 r6 2-Cl a23 r6 4-OtBu a25 r6 4-CO₂Me a26 r6 2-Cl a25 r6 4-OtBu a35 r6 4-CO₂Me a35 r6 2-Cl a26 r6 4-OtBu a25 r6 4-CO₂tBu a1 r6 3-Cl a35 r6 4-OtBu a35 r6 4-CO₂tBu a2 r6 3-Cl a1 r6 4-OCF₃ a25 r6 4-CH₂Ph a4 r6 3-Cl a2 r6 4-OCF₃ a35 r6 4-CH₂Ph a23 r6 3-Cl a4 r6 4-OCF₃ a25 r6 4-OCH₂Ph a25 r6 3-Cl a23 r6 4-OCF₃ a35 r6 4-OCH_(2Ph) a26 r6 3-Cl a25 r6 4-OCF₃ a25 r6 4-(2-thienyl) a35 r6 3-Cl a26 r6 4-OCF₃ a35 r6 4-(2-thienyl) a1 r6 2,4-F₂ a35 r6 4-OCF₃ a25 r6 4-(3-thienyl) a2 r6 2,4-F₂ a25 r6 4-SMe a35 r6 4-(3-thienyl) a4 r6 2,4-F₂ a35 r6 4-SMe a25 r6 4-(2-pyridyl) a23 r6 2,4-F₂ a25 r6 4-SOMe a35 r6 4-(2-pyridyl) a25 r6 2,4-F₂ a35 r6 4-SOMe a25 r6 4-(3-pyridyl) a26 r6 2,4-F₂ a25 r6 4-SO₂Me a35 r6 4-(3-pyridyl) a35 r6 2,4-F₂ a35 r6 4-SO₂Me a25 r6 4-(4-pyridyl) a1 r6 2,6-F₂ a25 r6 4-NHMe a35 r6 4-(4-pyridyl) a2 r6 2,6-F₂ a35 r6 4-NHMe a25 r6 4-Ph a4 r6 2,6-F₂ a25 r6 4-NMe₂ a35 r6 4-Ph a23 r6 2,6-F₂ a35 r6 4-NMe₂ a25 r6 4-(4-Cl-Ph) a25 r6 2,6-F₂ a25 r6 4-SiMe₄ a35 r6 4-(4-Cl-Ph) a26 r6 2,6-F₂ a35 r6 4-SiMe₄ a25 r6 4-(4-F-Ph) a35 r6 2,6-F₂ a25 r6 4-CH₂OEt a35 r6 4-(4-F-Ph) al r6 2,4-Cl₂ a35 r6 4-CH₂OEt a25 r6 4-OPh a2 r6 2,4-Cl₂ a25 r6 4-CH₂SEt a35 r6 4-OPh a4 r6 2,4-Cl₂ a35 r6 4-CH₂SEt a1 r6 2-Cl a23 r6 2,4-Cl₂ a25 r6 2,4-Cl₂ a1 r6 2-OEt-4-tBu a26 r6 2,4-Cl₂ a2 r6 2-OEt-4-tBu a35 r6 2,4-Cl₂ a4 r6 2-OEt-4-tBu a1 r6 2,6-Cl₂ a23 r6 2-OEt-4-tBu a2 r6 2,6-Cl₂ a25 r6 2-OEt-4-tBu a4 r6 2,6-Cl₂ a26 r6 2-OEt-4-tBu a23 r6 2,6-Cl₂ a35 r6 2-OEt-4-tBu a25 r6 2,6-Cl₂ a1 r6 4-(4-OCF₃-Ph) a26 r6 2,6-Cl₂ a2 r6 4-(4-OCF₃-Ph) a35 r6 2,6-Cl₂ a4 r6 4-(4-OCF₃-Ph) a1 r6 2,4,6-Cl₃ a23 r6 4-(4-OCF₃-Ph) a2 r6 2,4,6-Cl₃ a25 r6 4-(4-OCF₃-Ph) a4 r6 2,4,6-Cl₃ a26 r6 4-(4-OCF₃-Ph) a23 r6 2,4,6-Cl₃ a35 r6 4-(4-OCF₃-Ph) a25 r6 2,4,6-Cl₃ a1 r6 4-O-(2-pyridyl) a26 r6 2,4,6-Cl₃ a2 r6 4-O-(2-pyridyl) a35 r6 2,4,6-Cl₃ a4 r6 4-O-(2-pyridyl) a1 r6 2,3,4,5,6-F₅ a23 r6 4-O-(2-pyridyl) a2 r6 2,3,4,5,6-F₅ a25 r6 4-O-(2-pyridyl) a4 r6 2,3,4,5,6-F₅ a26 r6 4-O-(2-pyridyl) a23 r6 2,3,4,5,6-F₅ a35 r6 4-O-(2-pyridyl) a25 r6 2,3,4,5,6-F₅ a1 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a26 r6 2,3,4,5,6-F₅ a2 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a35 r6 2,3,4,5,6-F₅ a4 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a1 r6 2,3,4,5,6-Cl₅ a23 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a2 r6 2,3,4,5,6-Cl₅ a25 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a4 r6 2,3,4,5,6-Cl₅ a26 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a23 r6 2,3,4,5,6-Cl₅ a35 r6 4-O-(3-Cl-5-CF₃-pyridine-2-yl)- a25 r6 2,3,4,5,6-Cl₅ a26 r6 2,3,4,5,6-Cl₅ a35 r6 2,3,4,5,6-Cl₅ a1 r6 3-NO₂ a7 r6 3-F a26 r6 3-F a2 r6 3-NO₂ a8 r6 3-F a25 r7 3-F a4 r6 3-NO₂ a9 r6 3-F a25 r8 3-F a23 r6 3-NO₂ a10 r6 3-F a25 r9 3-F a25 r6 3-NO₂ a11 r6 3-F a25 r10 3-F a26 r6 3-NO₂ a12 r6 3-F a25 r1 3-F a35 r6 3-NO₂ a13 r6 3-F a25 r12 3-F a1 r6 3-CN a14 r6 3-F a25 n13 3-F a2 r6 3-CN a15 r6 3-F a25 r14 3-F a4 r6 3-CN a16 r6 3-F a25 r15 3-F a23 r6 3-CN a17 r6 3-F a25 r16 3-F a25 r6 3-CN a18 r6 3-F a25 n17 3-F a26 r6 3-CN a19 r6 3-F a25 r18 3-F a35 r6 3-CN a20 r6 3-F a25 n19 3-F a1 r1 3-F a21 r6 3-F a25 r20 3-F a1 r6 3-F a22 r6 3-F a25 r21 3-F a1 r22 3-F a23 r1 3-F a25 r22 3-F a1 r43 3-F a23 r6 3-F a25 r23 3-F a1 r52 3-F a23 r22 3-F a25 r24 3-F a2 r1 3-F a23 r43 3-F a25 r25 3-F a2 r6 3-F a23 r52 3-F a25 r26 3-F a2 r22 3-F a24 r1 3-F a25 r27 3-F a2 r43 3-F a24 r6 3-F a25 r28 3-F a2 r52 3-F a24 r22 3-F a25 r29 3-F a3 r6 3-F a24 r43 3-F a25 r30 3-F a3 r22 3-F a24 r52 3-F a25 r31 3-F a4 r6 3-F a25 r1 3-F a25 r32 3-F a4 r22 3-F a25 r2 3-F a25 r33 3-F a5 r6 3-F a25 r3 3-F a25 r34 3-F a5 r22 3-F a25 r4 3-F a25 r35 3-F a6 r6 3-F a25 r5 3-F a25 r36 3-F a26 r37 3-F a26 r1 3-F a32 r6 3-F a25 r38 3-F a26 r6 3-F a32 r22 3-F a25 r39 3-F a26 r22 3-F a32 r43 3-F a25 r40 3-F a26 r43 3-F a32 r52 3-F a25 r41 3-F a26 r52 3-F a33 r1 3-F a25 r42 3-F a27 r1 3-F a33 r6 3-F a25 r43 3-F a27 r6 3-F a33 r22 3-F a25 r44 3-F a27 r22 3-F a33 r43 3-F a25 r45 3-F a27 r43 3-F a33 r52 3-F a25 r46 3-F a27 r52 3-F a34 r1 3-F a25 r47 3-F a28 r1 3-F a34 r6 3-F a25 r48 3-F a28 r6 3-F a34 r22 3-F a25 r49 3-F a28 r22 3-F a34 r43 3-F a25 r50 3-F a28 r43 3-F a34 r52 3-F a25 r51 3-F a28 r52 3-F a35 r1 3-F a25 r52 3-F a29 r1 3-F a35 r6 3-F a25 r53 3-F a29 r6 3-F a35 r22 3-F a25 r54 3-F a29 r22 3-F a35 r43 3-F a25 r55 3-F a29 r43 3-F a35 r52 3-F a25 r56 3-F a29 r52 3-F a36 r1 3-F a25 r57 3-F a30 r1 3-F a36 r6 3-F a25 r58 3-F a30 r6 3-F a36 r22 3-F a25 r59 3-F a30 r22 3-F a36 r43 3-F a25 r60 3-F a30 r43 3-F a36 r52 3-F a25 r61 3-F a30 r52 3-F a37 r6 3-F a25 r62 3-F a31 r1 3-F a38 r1 3-F a25 r63 3-F a31 r6 3-F a38 r6 3-F a25 r64 3-F a31 r22 3-F a38 r22 3-F a25 r65 3-F a31 r43 3-F a38 r43 3-F a25 r66 3-F a31 r52 3-F a38 r52 3-F a25 r67 3-F a32 r1 3-F a39 r1 3-F a39 r6 3-F a1 r1 3-Cl a23 r43 3-Cl a39 r22 3-F a1 r22 3-Cl a23 r52 3-Cl a39 r43 3-F a1 r43 3-Cl a24 r1 3-Cl a39 r52 3-F a1 r52 3-Cl a24 r6 3-Cl a40 r1 3-F a2 r1 3-Cl a24 r22 3-Cl a40 r6 3-F a2 r22 3-Cl a24 r43 3-Cl a40 r22 3-F a2 r43 3-Cl a24 r52 3-Cl a40 r43 3-F a2 r52 3-Cl a25 r1 3-Cl a40 r52 3-F a3 r6 3-Cl a25 r2 3-Cl a41 r1 3-F a3 r22 3-Cl a25 r3 3-Cl a41 r6 3-F a4 r22 3-Cl a25 r4 3-Cl a41 r22 3-F a5 r6 3-Cl a25 r5 3-Cl a41 r43 3-F a5 r22 3-Cl a25 r7 3-Cl a41 r52 3-F a6 r6 3-Cl a25 r8 3-Cl a42 r6 3-F a7 r6 3-Cl a25 r9 3-Cl a43 r6 3-F a8 r6 3-Cl a25 r10 3-Cl a44 r6 3-F a9 r6 3-Cl a25 r1 3-Cl a45 r6 3-F a10 r6 3-Cl a25 n12 3-Cl a46 r6 3-F a11 r6 3-Cl a25 r13 3-Cl a47 r6 3-F a12 r6 3-Cl a25 n14 3-Cl a48 r6 3-F a13 r6 3-Cl a25 n15 3-Cl a49 r6 3-F a14 r6 3-Cl a25 n16 3-Cl a50 r6 3-F a15 r6 3-Cl a25 n17 3-Cl a51 r6 3-F a16 r6 3-Cl a25 n18 3-Cl a52 r6 3-F a17 r6 3-Cl a25 n19 3-Cl a53 r6 3-F a18 r6 3-Cl a25 r20 3-Cl a54 r6 3-F a19 r6 3-Cl a25 r21 3-Cl a55 r6 3-F a20 r6 3-Cl a25 r22 3-Cl a56 r6 3-F a21 r6 3-Cl a25 r23 3-Cl a57 r6 3-F a22 r6 3-Cl a25 r24 3-Cl a58 r6 3-F a23 r1 3-Cl a25 r25 3-Cl a59 r6 3-F a23 r22 3-Cl a25 r26 3-Cl a25 r27 3-Cl a25 r58 3-Cl a30 r22 3-Cl a25 r28 3-Cl a25 r59 3-Cl a30 r43 3-Cl a25 r29 3-Cl a25 r60 3-Cl a30 r52 3-Cl a25 r30 3-Cl a25 r61 3-Cl a31 r2 3-Cl a25 r31 3-Cl a25 r62 3-Cl a31 r6 3-Cl a25 r32 3-Cl a25 r63 3-Cl a31 r22 3-Cl a25 r33 3-Cl a25 r64 3-Cl a31 r43 3-Cl a25 r34 3-Cl a25 r65 3-Cl a31 r52 3-Cl a25 r35 3-Cl a25 r66 3-Cl a32 r1 3-Cl a25 r36 3-Cl a25 r67 3-Cl a32 r6 3-Cl a25 r37 3-Cl a26 r1 3-Cl a32 r22 3-Cl a25 r38 3-Cl a26 r22 3-Cl a32 r43 3-Cl a25 r39 3-Cl a26 r43 3-Cl a32 r52 3-Cl a25 r40 3-Cl a26 r52 3-Cl a33 r1 3-Cl a25 r41 3-Cl a27 r1 3-Cl a33 r6 3-Cl a25 r42 3-Cl a27 r6 3-Cl a33 r22 3-Cl a25 r43 3-Cl a27 r22 3-Cl a33 r43 3-Cl a25 r44 3-Cl a27 r43 3-Cl a33 r62 3-Cl a25 r45 3-Cl a27 r52 3-Cl a34 r1 3-Cl a25 r46 3-Cl a28 r1 3-Cl a34 r6 3-Cl a25 r47 3-Cl a28 r6 3-Cl a34 r22 3-Cl a25 r48 3-Cl a28 r22 3-Cl a34 r43 3-Cl a26 r49 3-Cl a28 r43 3-Cl a34 r52 3-Cl a25 r50 3-Cl a28 r52 3-Cl a35 r1 3-Cl a25 r51 3-Cl a29 r1 3-Cl a35 r22 3-Cl a25 r52 3-Cl a29 r6 3-Cl a35 r43 3-Cl a25 r53 3-Cl a29 r22 3-Cl a35 r52 3-Cl a25 r54 3-Cl a29 r43 3-Cl a36 r1 3-Cl a25 r55 3-Cl a29 r52 3-Cl a36 r6 3-Cl a25 r56 3-Cl a30 r1 3-Cl a36 r22 3-Cl a25 r57 3-Cl a30 r6 3-Cl a36 r43 3-Cl a36 r52 3-Cl a52 r6 3-Cl a23 r6 3-iPr a37 r6 3-Cl a53 r6 3-Cl a25 r6 3-iPr a38 r1 3-Cl a54 r6 3-Cl a26 r6 3-iPr a38 r6 3-Cl a55 r6 3-Cl a35 r6 3-iPr a38 r22 3-Cl a56 r6 3-Cl a1 r6 3-tBu a38 r43 3-Cl a57 r6 3-Cl a2 r6 3-tBu a38 r52 3-Cl a58 r6 3-Cl a4 r6 3-tBu a39 r1 3-Cl a59 r6 3-Cl a23 r6 3-tBu a39 r6 3-Cl al r6 3-Br a25 r6 3-tBu a39 r22 3-Cl a2 r6 3-Br a26 r6 3-tBu a39 r43 3-Cl a4 r6 3-Br a35 r6 3-tBu a39 r52 3-Cl a23 r6 3-Br a1 r6 3-nHex a40 r1 3-Cl a25 r6 3-Br a2 r6 3-nHex a40 r6 3-Cl a26 r6 3-Br a4 r6 3-nHex a40 r22 3-Cl a35 r6 3-Br a23 r6 3-nHex a40 r43 3-Cl a1 r6 3-I a25 r6 3-nHex a40 r52 3-Cl a2 r6 3-I a26 r6 3-nHex a41 r1 3-Cl a4 r6 3-I a35 r6 3-nHex a41 r6 3-Cl a23 r6 3-I a1 r6 3-cPr a41 r22 3-Cl a25 r6 3-I a2 r6 3-cPr a41 r43 3-Cl a26 r6 3-I a4 r6 3-cPr a41 r52 3-Cl a35 r6 3-I a23 r6 3-cPr a42 r6 3-Cl a1 r6 3-Me a25 r6 3-cPr a43 r6 3-Cl a2 r6 3-Me a26 r6 3-cPr a44 r6 3-Cl a4 r6 3-Me a35 r6 3-cPr a45 r6 3-Cl a23 r6 3-Me a1 r6 3-cHex a46 r6 3-Cl a25 r6 3-Me a2 r6 3-cHex a47 r6 3-Cl a26 r6 3-Me a4 r6 3-cHex a48 r6 3-Cl a35 r6 3-Me a23 r6 3-cHex a49 r6 3-Cl a1 r6 3-iPr a25 r6 3-cHex a50 r6 3-Cl a2 r6 3-iPr a26 r6 3-cHex a51 r6 3-Cl a4 r6 3-iPr a35 r6 3-cHex a1 r1 3-CF₃ a21 r6 3-CF₃ a25 r20 3-CF₃ a1 r6 3-CF₃ a22 r6 3-CF₃ a25 r21 3-CF₃ a1 r22 3-CF₃ a23 r1 3-CF₃ a25 r22 3-CF₃ a1 r43 3-CF₃ a23 r6 3-CF₃ a25 r23 3-CF₃ a1 r52 3-CF₃ a23 r22 3-CF₃ a25 r24 3-CF₃ a2 ri 3-CF₃ a23 r43 3-CF₃ a25 r25 3-CF₃ a2 r6 3-CF₃ a23 r52 3-CF₃ a25 r26 3-CF₃ a2 r22 3-CF₃ a24 r1 3-CF₃ a25 r27 3-CF₃ a2 r43 3-CF₃ a24 r6 3-CF₃ a25 r28 3-CF₃ a2 r52 3-CF₃ a24 r22 3-CF₃ a25 r29 3-CF₃ a3 r6 3-CF₃ a24 r43 3-CF₃ a25 r30 3-CF₃ a3 r22 3-CF₃ a24 r52 3-CF₃ a25 r31 3-CF₃ a4 r6 3-CF₃ a25 r1 3-CF₃ a25 r32 3-CF₃ a4 r22 3-CF₃ a25 r2 3-CF₃ a25 r33 3-CF₃ a5 r6 3-CF₃ a25 r3 3-CF₃ a25 r34 3-CF₃ a6 r22 3-CF₃ a25 r4 3-CF₃ a25 r35 3-CF₃ a6 r6 3-CF₃ a25 r5 3-CF₃ a25 r36 3-CF₃ a7 r6 3-CF₃ a25 r6 3-CF₃ a25 r37 3-CF₃ a8 r6 3-CF₃ a25 r7 3-CF₃ a25 r38 3-CF₃ a9 r6 3-CF₃ a25 r8 3-CF₃ a25 r39 3-CF₃ a10 r6 3-CF₃ a25 r9 3-CF₃ a25 r40 3-CF₃ a11 r6 3-CF₃ a25 r10 3-CF₃ a25 r41 3-CF₃ a12 r6 3-CF₃ a25 r1 3-CF₃ a25 r42 3-CF₃ a13 r6 3-CF₃ a25 r12 3-CF₃ a25 r43 3-CF₃ a14 r6 3-CF₃ a25 r13 3-CF₃ a25 r44 3-CF₃ a15 r6 3-CF₃ a25 n14 3-CF₃ a25 r45 3-CF₃ a16 r6 3-CF₃ a25 n15 3-CF₃ a25 r46 3-CF₃ a17 r6 3-CF₃ a25 r16 3-CF₃ a25 r47 3-CF₃ a18 r6 3-CF₃ a25 r17 3-CF₃ a25 r48 3-CF₃ a19 r6 3-CF₃ a25 r18 3-CF₃ a25 r49 3-CF₃ a20 r6 3-CF₃ a25 r19 3-CF₃ a25 r50 3-CF₃ a25 r51 3-CF₃ a29 r1 3-CF₃ a35 r22 3-CF₃ a25 r52 3-CF₃ a29 r6 3-CF₃ a36 r43 3-CF₃ a25 r53 3-CF₃ a29 r22 3-CF₃ a35 r52 3-CF₃ a25 r54 3-CF₃ a29 r43 3-CF₃ a36 r1 3-CF₃ a25 r55 3-CF₃ a29 r52 3-CF₃ a36 r6 3-CF₃ a25 r56 3-CF₃ a30 r1 3-CF₃ a36 r22 3-CF₃ a25 r57 3-CF₃ a30 r6 3-CF₃ a36 r43 3-CF₃ a25 r58 3-CF₃ a30 r22 3-CF₃ a36 r52 3-CF₃ a25 r59 3-CF₃ a30 r43 3-CF₃ a37 r6 3-CF₃ a25 r60 3-CF₃ a30 r52 3-CF₃ a38 r1 3-CF₃ a25 r61 3-CF₃ a31 r1 3-CF₃ a38 r6 3-CF₃ a25 r62 3-CF₃ a31 r6 3-CF₃ a38 r22 3-CF₃ a25 r63 3-CF₃ a31 r22 3-CF₃ a38 r43 3-CF₃ a25 r64 3-CF₃ a31 r43 3-CF₃ a38 r52 3-CF₃ a25 r65 3-CF₃ a31 r52 3-CF₃ a39 r1 3-CF₃ a25 r66 3-CF₃ a32 r1 3-CF₃ a39 r6 3-CF₃ a25 r67 3-CF₃ a32 r6 3-CF₃ a39 r22 3-CF₃ a26 r1 3-CF₃ a32 r22 3-CF₃ a39 r43 3-CF₃ a26 r6 3-CF₃ a32 r43 3-CF₃ a39 r52 3-CF₃ a26 r22 3-CF₃ a32 r52 3-CF₃ a40 r1 3-CF₃ a26 r43 3-CF₃ a33 r1 3-CF₃ a40 r6 3-CF₃ a26 r52 3-CF₃ a33 r6 3-CF₃ a40 r22 3-CF₃ a27 r1 3-CF₃ a33 r22 3-CF₃ a40 r43 3-CF₃ a27 r6 3-CF₃ a33 r43 3-CF₃ a40 r52 3-CF₃ a27 r22 3-CF₃ a33 r52 3-CF₃ a41 r1 3-CF₃ a27 r43 3-CF₃ a34 r1 3-CF₃ a41 r6 3-CF₃ a27 r52 3-CF₃ a34 r6 3-CF₃ a41 r22 3-CF₃ a28 r1 3-CF₃ a34 r22 3-CF₃ a41 r43 3-CF₃ a28 r6 3-CF₃ a34 r43 3-CF₃ a41 r52 3-CF₃ a28 r22 3-CF₃ a34 r52 3-CF₃ a42 r6 3-CF₃ a28 r43 3-CF₃ a35 r1 3-CF₃ a43 r6 3-CF₃ a28 r52 4-CF₃ a35 r6 4-CF₃ a44 r6 4-CF₃ a45 r6 3-CF₃ a23 r6 3-OtBu a35 r6 3-CO₂Me a46 r6 3-CF₃ a25 r6 3-OtBu a25 r6 3-CO₂tBu a47 r6 3-CF₃ a26 r6 3-OtBu a35 r6 3-CO₂tBu a48 r6 3-CF₃ a35 r6 3-OtBu a25 r6 3-CH₂Ph a49 r6 3-CF₃ a1 r6 3-OCF₃ a35 r6 3-CH₂Ph a50 r6 3-CF₃ a2 r6 3-OCF₃ a25 r6 3-OCH₂Ph a51 r6 3-CF₃ a4 r6 3-OCF₃ a35 r6 3-OCH₂Ph a52 r6 3-CF₃ a23 r6 3-OCF₃ a25 r6 3-(2-thienyl) a53 r6 3-CF₃ a25 r6 3-OCF₃ a35 r6 3-(2-thienyl) a54 r6 3-CF₃ a26 r6 3-OCF₃ a25 r6 3-(3-thienyl) a55 r6 3-CF₃ a35 r6 3-OCF₃ a35 r6 3-(3-thienyl) a56 r6 3-CF₃ a25 r6 3-Sine a25 r6 3-(2-pyridyl) a57 r6 3-CF₃ a35 r6 3-Sine a35 r6 3-(2-pyridyl) a58 r6 3-CF₃ a25 r6 3-SOMe a25 r6 3-(3-pyridyl) a59 r6 3-CF₃ a35 r6 3-SOMe a35 r6 3-(3-pyridyl) a1 r6 3-OMe a25 r6 3-SO₂Me a25 r6 3-(4-pyridyl) a2 r6 3-OMe a35 r6 3-SO_(2Me) a35 r6 3-(4-pyridyl) a4 r6 3-OMe a25 r6 3-NHMe a25 r6 3-Ph a23 r6 3-OMe a35 r6 3-NHMe a35 r6 3-Ph a25 r6 3-OMe a25 r6 3-NMe₂ a25 r6 3-(4-Cl—Ph) a26 r6 3-OMe a35 r6 3-NMe₂ a35 r6 3-(4-Cl—Ph) a35 r6 3-OMe a25 r6 3-SiMe₄ a25 r6 3-(4-F—Ph) a1 r6 3-OiPr a35 r6 3-SiMe₄ a35 r6 3-(4-F—Ph) a2 r6 3-OiPr a25 r6 3-CH₂OEt a25 r6 3-OPh a4 r6 3-OiPr a35 r6 3-CH₂OEt a35 r6 3-OPh a23 r6 3-OiPr a25 r6 3-CH₂Set a1 r1 3,5-Cl₂ a25 r6 3-OiPr a35 r6 3-CH₂Set a1 r6 3,5-Cl₂ a26 r6 3-OiPr a25 r6 3-COMe a1 r22 3,5-Cl₂ a35 r6 3-OiPr a35 r6 3-COMe a1 r43 3,5-Cl₂ a1 r6 3-OtBu a25 r6 3-CotBu a1 r52 3,5-Cl₂ a2 r6 3-OtBu a35 r6 3-CotBu a2 r1 3,5-Cl₂ a4 r6 3-OtBu a25 r6 3-CO₂Me a2 r6 3,5-Cl₂ a2 r22 3,5-Cl₂ a24 r1 3,5-Cl₂ a25 r27 3,5-Cl₂ a2 r43 3,5-Cl₂ a24 r6 3,5-Cl₂ a25 r28 3,5-Cl₂ a2 r52 3,5-Cl₂ a24 r22 3,5-Cl₂ a25 r29 3,5-Cl₂ a3 r6 3,5-Cl₂ a24 r43 3,5-Cl₂ a25 r30 3,5-Cl₂ a3 r22 3,5-Cl₂ a24 r52 3,5-Cl₂ a25 r31 3,5-Cl₂ a4 r6 3,5-Cl₂ a25 r1 3,5-Cl₂ a25 r32 3,5-Cl₂ a4 r22 3,5-Cl₂ a25 r2 3,5-Cl₂ a25 r33 3,5-Cl₂ a5 r6 3,5-Cl₂ a25 r3 3,5-Cl₂ a25 r34 3,5-Cl₂ a6 r22 3,5-Cl₂ a25 r4 3,5-Cl₂ a25 r35 3,5-Cl₂ a6 r6 3,5-Cl₂ a25 r5 3,5-Cl₂ a25 r36 3,5-Cl₂ a7 r6 3,5-Cl₂ a25 r6 3,5-Cl₂ a25 r37 3,5-Cl₂ a8 r6 3,5-Cl₂ a25 r7 3,5-Cl₂ a25 r38 3,5-Cl₂ a9 r6 3,5-Cl₂ a25 r8 3,5-Cl₂ a25 r39 3,5-Cl₂ a10 r6 3,5-Cl₂ a25 r9 3,5-Cl₂ a25 r40 3,5-Cl₂ a11 r6 3,5-Cl₂ a25 r10 3,5-Cl₂ a25 r41 3,5-Cl₂ a12 r6 3,5-Cl₂ a25 r1 3,5-Cl₂ a25 r42 3,5-Cl₂ a13 r6 3,5-Cl₂ a25 r12 3,5-Cl₂ a25 r43 3,5-Cl₂ a14 r6 3,5-Cl₂ a25 r13 3,5-Cl₂ a25 r44 3,5-Cl₂ a15 r6 3,5-Cl₂ a25 r14 3,5-Cl₂ a25 r45 3,5-Cl₂ a16 r6 3,5-Cl₂ a25 r15 3,5-Cl₂ a25 r46 3,5-Cl₂ a17 r6 3,5-Cl₂ a25 r16 3,5-Cl₂ a25 r47 3,5-Cl₂ a18 r6 3,5-Cl₂ a25 r17 3,5-Cl₂ a25 r48 3,5-Cl₂ a19 r6 3,5-Cl₂ a25 r18 3,5-Cl₂ a25 r49 3,5-Cl₂ a20 r6 3,5-Cl₂ a25 r19 3,5-Cl₂ a25 r50 3,5-Cl₂ a21 r6 3,5-Cl₂ a25 r20 3,5-Cl₂ a25 r51 3,5-Cl₂ a22 r6 3,5-Cl₂ a25 r21 3,5-Cl₂ a25 r52 3,5-Cl₂ a23 r1 3,5-Cl₂ a25 r22 3,5-Cl₂ a25 r53 3,5-Cl₂ a23 r6 3,5-Cl₂ a25 r23 3,5-Cl₂ a25 r54 3,5-Cl₂ a23 r22 3,5-Cl₂ a25 r24 3,5-Cl₂ a25 r55 3,5-Cl₂ a23 r43 3,5-Cl₂ a25 r25 3,5-Cl₂ a25 r56 3,5-Cl₂ a23 r52 3,5-Cl₂ a25 r26 3,5-Cl₂ a25 r57 3,5-Cl₂ a25 r58 3,5-Cl₂ a30 r22 3,5-Cl₂ a36 r52 3,5-Cl₂ a25 r59 3,5-Cl₂ a30 r43 3,5-Cl₂ a37 r6 3,5-Cl₂ a25 r60 3,5-Cl₂ a30 r52 3,5-Cl₂ a38 r1 3,5-Cl₂ a25 r61 3,5-Cl₂ a31 r1 3,5-Cl₂ a38 r6 3,5-Cl₂ a25 r62 3,5-Cl₂ a31 r6 3,5-Cl₂ a38 r22 3,5-Cl₂ a25 r63 3,5-Cl₂ a31 r22 3,5-Cl₂ a38 r43 3,5-Cl₂ a25 r64 3,5-Cl₂ a31 r43 3,5-Cl₂ a38 r52 3,5-Cl₂ a25 r65 3,5-Cl₂ a31 r52 3,5-Cl₂ a39 r1 3,5-Cl₂ a25 r66 3,5-Cl₂ a32 r1 3,5-Cl₂ a39 r6 3,5-Cl₂ a25 r67 3,5-Cl₂ a32 r6 3,5-Cl₂ a39 r22 3,5-Cl₂ a26 r1 3,5-Cl₂ a32 r22 3,5-Cl₂ a39 r43 3,5-Cl₂ a26 r6 3,5-Cl₂ a32 r43 3,5-Cl₂ a39 r52 3,5-Cl₂ a26 r22 3,5-Cl₂ a32 r52 3,5-Cl₂ a40 r1 3,5-Cl₂ a26 r43 3,5-Cl₂ a33 r1 3,5-Cl₂ a40 r6 3,5-Cl₂ a26 r52 3,5-Cl₂ a33 r6 3,5-Cl₂ a40 r22 3,5-Cl₂ a27 r1 3,5-Cl₂ a33 r22 3,5-Cl₂ a40 r43 3,5-Cl₂ a27 r6 3,5-Cl₂ a33 r43 3,5-Cl₂ a40 r52 3,5-Cl₂ a27 r22 3,5-Cl₂ a33 r52 3,5-Cl₂ a41 r1 3,5-Cl₂ a27 r43 3,5-Cl₂ a34 r1 3,5-Cl₂ a41 r6 3,5-Cl₂ a27 r52 3,5-Cl₂ a34 r6 3,5-Cl₂ a41 r22 3,5-Cl₂ a28 r1 3,5-Cl₂ a34 r22 3,5-Cl₂ a41 r43 3,5-Cl₂ a28 r6 3,5-Cl₂ a34 r43 3,5-Cl₂ a41 r52 3,5-Cl₂ a28 r22 3,5-Cl₂ a34 r52 3,5-Cl₂ a42 r6 3,5-Cl₂ a28 r43 3,5-Cl₂ a35 r1 3,5-Cl₂ a43 r6 3,5-Cl₂ a28 r52 3,5-Cl₂ a35 r6 3,5-Cl₂ a44 r6 3,5-Cl₂ a29 r1 3,5-Cl₂ a35 r22 3,5-Cl₂ a45 r6 3,5-Cl₂ a29 r6 3,5-Cl₂ a35 r43 3,5-Cl₂ a46 r6 3,5-Cl₂ a29 r22 3,5-Cl₂ a35 r52 3,5-Cl₂ a47 r6 3,5-Cl₂ a29 r43 3,5-Cl₂ a36 r1 3,5-Cl₂ a48 r6 3,5-Cl₂ a29 r52 3,5-Cl₂ a36 r6 3,5-Cl₂ a49 r6 3,5-Cl₂ a30 r1 3,5-Cl₂ a36 r22 3,5-Cl₂ a50 r6 3,5-Cl₂ a52 r6 3,5-Cl₂ a14 r6 3,5-F₂ a25 r14 3,5-F₂ a53 r6 3,5-Cl₂ a15 r6 3,5-F₂ a25 r15 3,5-F₂ a54 r6 3,5-Cl₂ a16 r6 3,5-F₂ a25 r16 3,5-F₂ a55 r6 3,5-Cl₂ a17 r6 3,5-F₂ a25 r17 3,5-F₂ a56 r6 3,5-Cl₂ a18 r6 3,5-F₂ a25 r18 3,5-F₂ a57 r6 3,5-Cl₂ a19 r6 3,5-F₂ a25 r19 3,5-F₂ a58 r6 3,5-Cl₂ a20 r6 3,5-F₂ a25 r20 3,5-F₂ a59 r6 3,5-Cl₂ a21 r6 3,5-F₂ a25 r21 3,5-F₂ a1 r1 3,5-F₂ a22 r6 3,5-F₂ a25 r22 3,5-F₂ a1 r6 3,5-F₂ a23 r1 3,5-F₂ a25 r23 3,5-F₂ a1 r22 3,5-F₂ a23 r6 3,5-F₂ a25 r24 3,5-F₂ a1 r43 3,5-F₂ a23 r22 3,5-F₂ a25 r25 3,5-F₂ a1 r52 3,5-F₂ a23 r43 3,5-F₂ a25 r26 3,5-F₂ a2 r1 3,5-F₂ a23 r52 3,5-F₂ a25 r27 3,5-F₂ a2 r6 3,5-F₂ a24 r1 3,5-F₂ a25 r28 3,5-F₂ a2 r22 3,5-F₂ a24 r6 3,5-F₂ a25 r29 3,5-F₂ a2 r43 3,5-F₂ a24 r22 3,5-F₂ a25 r30 3,5-F₂ a2 r52 3,5-F₂ a24 r43 3,5-F₂ a25 r31 3,5-F₂ a3 r6 3,5-F₂ a24 r52 3,5-F₂ a25 r32 3,5-F₂ a3 r22 3,5-F₂ a25 r1 3,5-F₂ a25 r33 3,5-F₂ a4 r6 3,5-F₂ a25 r2 3,5-F₂ a25 r34 3,5-F₂ a4 r22 3,5-F₂ a25 r3 3,5-F₂ a25 r35 3,5-F₂ a5 r6 3,5-F₂ a25 r4 3,5-F₂ a25 r36 3,5-F₂ a5 r22 3,5-F₂ a25 r5 3,5-F₂ a25 r37 3,5-F₂ a6 r6 3,5-F₂ a25 r6 3,5-F₂ a25 r38 3,5-F₂ a7 r6 3,5-F₂ a25 r7 3,5-F₂ a25 r39 3,5-F₂ a8 r6 3,5-F₂ a25 r8 3,5-F₂ a25 r40 3,5-F₂ a9 r6 3,5-F₂ a25 r9 3,5-F₂ a25 r41 3,5-F₂ a10 r6 3,5-F₂ a25 r10 3,5-F₂ a25 r42 3,5-F₂ a11 r6 3,5-F₂ a25 r1 3,5-F₂ a25 r43 3,5-F₂ a12 r6 3,5-F₂ a25 r12 3,5-F₂ a25 r44 3,5-F₂ a13 r6 3,5-F₂ a25 r13 3,5-F₂ a25 r45 3,5-F₂ a25 r46 3,5-F₂ a28 r1 3,5-F₂ a34 r22 3,5-F₂ a25 r47 3,5-F₂ a28 r6 3,5-F₂ a34 r43 3,5-F₂ a25 r48 3,5-F₂ a28 r22 3,5-F₂ a34 r52 3,5-F₂ a25 r49 3,5-F₂ a28 r43 3,5-F₂ a35 r1 3,5-F₂ a25 r50 3,5-F₂ a28 r52 3,5-F₂ a35 r6 3,5-F₂ a25 r51 3,5-F₂ a29 r1 3,5-F₂ a35 r22 3,5-F₂ a25 r52 3,5-F₂ a29 r6 3,5-F₂ a35 r43 3,5-F₂ a25 r53 3,5-F₂ a29 r22 3,5-F₂ a35 r52 3,5-F₂ a25 r54 3,5-F₂ a29 r43 3,5-F₂ a36 r1 3,5-F₂ a25 r55 3,5-F₂ a29 r52 3,5-F₂ a36 r6 3,5-F₂ a25 r56 3,5-F₂ a30 r1 3,5-F₂ a36 r22 3,5-F₂ a25 r57 3,5-F₂ a30 r6 3,5-F₂ a36 r43 3,5-F₂ a25 r58 3,5-F₂ a30 r22 3,5-F₂ a36 r52 3,5-F₂ a25 r59 3,5-F₂ a30 r43 3,5-F₂ a37 r6 3,5-F₂ a25 r60 3,5-F₂ a30 r52 3,5-F₂ a38 r1 3,5-F₂ a25 r61 3,5-F₂ a31 r1 3,5-F₂ a38 r6 3,5-F₂ a25 r62 3,5-F₂ a31 r6 3,5-F₂ a38 r22 3,5-F₂ a25 r63 3,5-F₂ a31 r22 3,5-F₂ a38 r43 3,5-F₂ a25 r64 3,5-F₂ a31 r43 3,5-F₂ a38 r52 3,5-F₂ a25 r65 3,5-F₂ a31 r52 3,5-F₂ a39 r1 3,5-F₂ a25 r66 3,5-F₂ a32 r1 3,5-F₂ a39 r6 3,5-F₂ a25 r67 3,5-F₂ a32 r6 3,5-F₂ a39 r22 3,5-F₂ a26 r1 3,5-F₂ a32 r22 3,5-F₂ a39 r43 3,5-F₂ a26 r6 3,5-F₂ a32 r43 3,5-F₂ a39 r52 3,5-F₂ a26 r22 3,5-F₂ a32 r52 3,5-F₂ a40 r1 3,5-F₂ a26 r43 3,5-F₂ a33 r1 3,5-F₂ a40 r6 3,5-F₂ a26 r52 3,5-F₂ a33 r6 3,5-F₂ a40 r22 3,5-F₂ a27 r1 3,5-F₂ a33 r22 3,5-F₂ a40 r43 3,5-F₂ a27 r6 3,5-F₂ a33 r43 3,5-F₂ a40 r52 3,5-F₂ a27 r22 3,5-F₂ a33 r52 3,5-F₂ a41 r1 3,5-F₂ a27 r43 3,5-F₂ a34 r1 3,5-F₂ a41 r6 3,5-F₂ a27 r52 3,5-F₂ a34 r6 3,5-F₂ a41 r22 3,5-F₂ a41 r43 3,5-F₂ a4 r6 3,5-Me₂ a25 r2 3,5-Me₂ a41 r52 3,5-F₂ a4 r22 3,5-Me₂ a25 r3 3,5-Me₂ a42 r6 3,5-F₂ a5 r6 3,5-Me₂ a25 r4 3,5-Me₂ a43 r6 3,5-F₂ a5 r22 3,5-Me₂ a25 r5 3,5-Me₂ a44 r6 3,5-F₂ a6 r6 3,5-Me₂ a25 r6 3,5-Me₂ a45 r6 3,5-F₂ a7 r6 3,5-Me₂ a25 r7 3,5-Me₂ a46 r6 3,5-F₂ a8 r6 3,5-Me₂ a25 r8 3,5-Me₂ a47 r6 3,5-F₂ a9 r6 3,5-Me₂ a25 r9 3,5-Me₂ a48 r6 3,5-F₂ a10 r6 3,5-Me₂ a25 r10 3,5-Me₂ a49 r6 3,5-F₂ a11 r6 3,5-Me₂ a25 r1 3,5-Me₂ a50 r6 3,5-F₂ a12 r6 3,5-Me₂ a25 r12 3,5-Me₂ a51 r6 3,5-F₂ a13 r6 3,5-Me₂ a25 r13 3,5-Me₂ a52 r6 3,5-F₂ a14 r6 3,5-Me₂ a25 n14 3,5-Me₂ a53 r6 3,5-F₂ a15 r6 3,5-Me₂ a25 n15 3,5-Me₂ a54 r6 3,5-F₂ a16 r6 3,5-Me₂ a25 r16 3,5-Me₂ a55 r6 3,5-F₂ a17 r6 3,5-Me₂ a25 r17 3,5-Me₂ a56 r6 3,5-F₂ a18 r6 3,5-Me₂ a25 r18 3,5-Me₂ a57 r6 3,5-F₂ a19 r6 3,5-Me₂ a25 r19 3,5-Me₂ a58 r6 3,5-F₂ a20 r6 3,5-Me₂ a25 r20 3,5-Me₂ a59 r6 3,5-F₂ a21 r6 3,5-Me₂ a25 r21 3,5-Me₂ a1 r1 3,5-Me₂ a22 r6 3,5-Me₂ a25 r22 3,5-Me₂ a1 r6 3,5-Me₂ a23 r1 3,5-Me₂ a25 r23 3,5-Me₂ a1 r22 3,5-Me₂ a23 r6 3,5-Me₂ a25 r24 3,5-Me₂ a1 r43 3,5-Me₂ a23 r22 3,5-Me₂ a25 r25 3,5-Me₂ a1 r52 3,5-Me₂ a23 r43 3,5-Me₂ a25 r26 3,5-Me₂ a2 r1 3,5-Me₂ a23 r52 3,5-Me₂ a25 r27 3,5-Me₂ a2 r6 3,5-Me₂ a24 r1 3,5-Me₂ a25 r28 3,5-Me₂ a2 r22 3,5-Me₂ a24 r6 3,5-Me₂ a25 r29 3,5-Me₂ a2 r43 3,5-Me₂ a24 r22 3,5-Me₂ a25 r30 3,5-Me₂ a2 r52 3,5-Me₂ a24 r43 3,5-Me₂ a25 r31 3,5-Me₂ a3 r6 3,5-Me₂ a24 r52 3,5-Me₂ a25 r32 3,5-Me₂ a3 r22 3,5-Me₂ a25 r1 3,5-Me₂ a25 r33 3,5-Me₂ a25 r34 3,5-Me₂ a25 r66 3,5-Me₂ a32 r1 3,5-Me₂ a25 r35 3,5-Me₂ a25 r67 3,5-Me₂ a32 r6 3,5-Me₂ a25 r36 3,5-Me₂ a26 r1 3,5-Me₂ a32 r22 3,5-Me₂ a25 r37 3,5-Me₂ a26 r6 3,5-Me₂ a32 r43 3,5-Me₂ a25 r38 3,5-Me₂ a26 r22 3,5-Me₂ a32 r52 3,5-Me₂ a25 r39 3,5-Me₂ a26 r43 3,5-Me₂ a33 r1 3,5-Me₂ a25 r40 3,5-Me₂ a26 r52 3,5-Me₂ a33 r6 3,5-Me₂ a25 r41 3,5-Me₂ a27 r1 3,5-Me₂ a33 r22 3,5-Me₂ a25 r42 3,5-Me₂ a27 r6 3,5-Me₂ a33 r43 3,5-Me₂ a25 r43 3,5-Me₂ a27 r22 3,5-Me₂ a33 r52 3,5-Me₂ a25 r44 3,5-Me₂ a27 r43 3,5-Me₂ a34 r1 3,5-Me₂ a25 r45 3,5-Me₂ a27 r52 3,5-Me₂ a34 r6 3,5-Me₂ a25 r46 3,5-Me₂ a28 r1 3,5-Me₂ a34 r22 3,5-Me₂ a25 r47 3,5-Me₂ a28 r6 3,5-Me₂ a34 r43 3,5-Me₂ a25 r48 3,5-Me₂ a28 r22 3,5-Me₂ a34 r52 3,5-Me₂ a25 r49 3,5-Me₂ a28 r43 3,5-Me₂ a35 r1 3,5-Me₂ a25 r50 3,5-Me₂ a28 r52 3,5-Me₂ a35 r6 3,5-Me₂ a25 r51 3,5-Me₂ a29 r1 3,5-Me₂ a35 r22 3,5-Me₂ a25 r52 3,5-Me₂ a29 r6 3,5-Me₂ a35 r43 3,5-Me₂ a25 r53 3,5-Me₂ a29 r22 3,5-Me₂ a35 r52 3,5-Me₂ a25 r54 3,5-Me₂ a29 r43 3,5-Me₂ a36 r1 3,5-Me₂ a25 r55 3,5-Me₂ a29 r52 3,5-Me₂ a36 r6 3,5-Me₂ a25 r56 3,5-Me₂ a30 r1 3,5-Me₂ a36 r22 3,5-Me₂ a25 r57 3,5-Me₂ a30 r6 3,5-Me₂ a36 r43 3,5-Me₂ a25 r58 3,5-Me₂ a30 r22 3,5-Me₂ a36 r52 3,5-Me₂ a25 r59 3,5-Me₂ a30 r43 3,5-Me₂ a37 r6 3,5-Me₂ a25 r60 3,5-Me₂ a30 r52 3,5-Me₂ a38 r1 3,5-Me₂ a25 r61 3,5-Me₂ a31 r1 3,5-Me₂ a38 r6 3,5-Me₂ a25 r62 3,5-Me₂ a31 r6 3,5-Me₂ a38 r22 3,5-Me₂ a25 r63 3,5-Me₂ a31 r22 3,5-Me₂ a38 r43 3,5-Me₂ a25 r64 3,5-Me₂ a31 r43 3,5-Me₂ a38 r52 3,5-Me₂ a25 r65 3,5-Me₂ a31 r52 3,5-Me₂ a39 r1 3,5-Me₂ a39 r6 3,5-Me₂ a1 H a12 H 4-F a39 r22 3,5-Me₂ a2 H a13 H 4-F a39 r43 3,5-Me₂ a4 H a14 H 4-F a39 r52 3,5-Me₂ a23 H a15 H 4-F a40 r1 3,5-Me₂ a25 H a16 H 4-F a40 r6 3,5-Me₂ a26 H a17 H 4-F a40 r22 3,5-Me₂ a35 H a18 H 4-F a40 r43 3,5-Me₂ a1 H 4-NO₂ a19 H 4-F a40 r52 3,5-Me₂ a2 H 4-NO₂ a20 H 4-F a41 r1 3,5-Me₂ a4 H 4-NO₂ a21 H 4-F a41 r6 3,5-Me₂ a23 H 4-NO₂ a22 H 4-F a41 r22 3,5-Me₂ a25 H 4-NO₂ a23 H 4-F a41 r43 3,5-Me₂ a26 H 4-NO₂ a24 H 4-F a41 r52 3,5-Me₂ a35 H 4-NO₂ a25 H 4-F a42 r6 3,5-Me₂ a1 H 4-CN a26 H 4-F a43 r6 3,5-Me₂ a2 H 4-CN a27 H 4-F a44 r6 3,5-Me₂ a4 H 4-CN a28 H 4-F a45 r6 3,5-Me₂ a23 H 4-CN a29 H 4-F a46 r6 3,5-Me₂ a25 H 4-CN a30 H 4-F a47 r6 3,5-Me₂ a26 H 4-CN a31 H 4-F a48 r6 3,5-Me₂ a35 H 4-CN a32 H 4-F a49 r6 3,5-Me₂ a1 H 4-F a33 H 4-F a50 r6 3,5-Me₂ a2 H 4-F a34 H 4-F a51 r6 3,5-Me₂ a3 H 4-F a35 H 4-F a52 r6 3,5-Me₂ a4 H 4-F a36 H 4-F a53 r6 3,5-Me₂ a5 H 4-F a37 H 4-F a54 r6 3,5-Me₂ a6 H 4-F a38 H 4-F a55 r6 3,5-Me₂ a7 H 4-F a39 H 4-F a56 r6 3,5-Me₂ a8 H 4-F a40 H 4-F a57 r6 3,5-Me₂ a9 H 4-F a41 H 4-F a58 r6 3,5-Me₂ a10 H 4-F a42 H 4-F a59 r6 3,5-Me₂ a11 H 4-F a43 H 4-F a44 H 4-F a16 H 4-Cl a47 H 4-Cl a45 H 4-F a17 H 4-Cl a48 H 4-Cl a46 H 4-F a18 H 4-Cl a49 H 4-Cl a47 H 4-F a19 H 4-Cl a50 H 4-Cl a48 H 4-F a20 H 4-Cl a51 H 4-Cl a49 H 4-F a21 H 4-Cl a52 H 4-Cl a50 H 4-F a22 H 4-Cl a53 H 4-Cl a51 H 4-F a23 H 4-Cl a54 H 4-Cl a52 H 4-F a24 H 4-Cl a55 H 4-Cl a53 H 4-F a25 H 4-Cl a56 H 4-Cl a54 H 4-F a26 H 4-Cl a57 H 4-Cl a55 H 4-F a27 H 4-Cl a58 H 4-Cl a56 H 4-F a28 H 4-Cl a59 H 4-Cl a57 H 4-F a29 H 4-Cl a1 H 4-Br a58 H 4-F a30 H 4-Cl a2 H 4-Br a59 H 4-F a31 H 4-Cl a4 H 4-Br a1 H 4-Cl a32 H 4-Cl a23 H 4-Br a2 H 4-Cl a33 H 4-Cl a25 H 4-Br a3 H 4-Cl a34 H 4-Cl a26 H 4-Br a4 H 4-Cl a35 H 4-Cl a35 H 4-Br a5 H 4-Cl a36 H 4-Cl a1 H 4-I a6 H 4-Cl a37 H 4-Cl a2 H 4-I a7 H 4-Cl a38 H 4-Cl a4 H 4-I a8 H 4-Cl a39 H 4-Cl a23 H 4-I a9 H 4-Cl a40 H 4-Cl a25 H 4-I a10 H 4-Cl a41 H 4-Cl a26 H 4-I a11 H 4-Cl a42 H 4-Cl a35 H 4-I a12 H 4-Cl a43 H 4-Cl a1 H 4-Me a13 H 4-Cl a44 H 4-Cl a2 H 4-Me a14 H 4-Cl a45 H 4-Cl a4 H 4-Me a15 H 4-Cl a46 H 4-Cl a23 H 4-Me a25 H 4-Me al H 4-cHex a25 H 4-CF₃ a26 H 4-Me a2 H 4-cHex a26 H 4-CF₃ a35 H 4-Me a4 H 4-cHex a27 H 4-CF₃ a1 H 4-iPr a23 H 4-cHex a28 H 4-CF₃ a2 H 4-iPr a25 H 4-cHex a29 H 4-CF₃ a4 H 4-iPr a26 H 4-cHex a30 H 4-CF₃ a23 H 4-iPr a35 H 4-cHex a31 H 4-CF₃ a25 H 4-iPr a1 H 4-CF₃ a32 H 4-CF₃ a26 H 4-iPr a2 H 4-CF₃ a33 H 4-CF₃ a35 H 4-iPr a3 H 4-CF₃ a34 H 4-CF₃ a1 H 4-tBu a4 H 4-CF₃ a35 H 4-CF₃ a2 H 4-tBu a5 H 4-CF₃ a36 H 4-CF₃ a4 H 4-tBu a6 H 4-CF₃ a37 H 4-CF₃ a23 H 4-tBu a7 H 4-CF₃ a38 H 4-CF₃ a25 H 4-tBu a8 H 4-CF₃ a39 H 4-CF₃ a26 H 4-tBu a9 H 4-CF₃ a40 H 4-CF₃ a35 H 4-tBu a10 H 4-CF₃ a41 H 4-CF₃ a1 H 4-nHex a11 H 4-CF₃ a42 H 4-CF₃ a2 H 4-nHex a12 H 4-CF₃ a43 H 4-CF₃ a4 H 4-nHex a13 H 4-CF₃ a44 H 4-CF₃ a23 H 4-nHex a14 H 4-CF₃ a45 H 4-CF₃ a25 H 4-nHex a15 H 4-CF₃ a46 H 4-CF₃ a26 H 4-nHex a16 H 4-CF₃ a47 H 4-CF₃ a35 H 4-nHex a17 H 4-CF₃ a48 H 4-CF₃ a1 H 4-cPr a18 H 4-CF₃ a49 H 4-CF₃ a2 H 4-cPr a19 H 4-CF₃ a50 H 4-CF₃ a4 H 4-cPr a20 H 4-CF₃ a51 H 4-CF₃ a23 H 4-cPr a21 H 4-CF₃ a52 H 4-CF₃ a25 H 4-cPr a22 H 4-CF₃ a53 H 4-CF₃ a26 H 4-cPr a23 H 4-CF₃ a54 H 4-CF₃ a35 H 4-cPr a24 H 4-CF₃ a55 H 4-CF₃ a56 H 4-CF₃ a35 H 4-OCF₃ a25 H 4-(3-thienyl) a57 H 4-CF₃ a25 H 4-Sme a35 H 4-(3-thienyl) a58 H 4-CF₃ a35 H 4-Sme a25 H 4-(2-pyridyl) a59 H 4-CF₃ a25 H 4-SOMe a35 H 4-(2-pyridyl) a1 H 4-OMe a35 H 4-SOMe a25 H 4-(3-pyridyl) a2 H 4-OMe a25 H 4-SO₂Me a35 H 4-(3-pyridyl) a4 H 4-OMe a35 H 4-SO₂Me a25 H 4-(4-pyridyl) a23 H 4-OMe a25 H 4-NHMe a35 H 4-(4-pyridyl) a25 H 4-OMe a35 H 4-NHMe a25 H 4-Ph a26 H 4-OMe a25 H 4-NMe₂ a35 H 4-Ph a35 H 4-OMe a35 H 4-NMe₂ a25 H 4-(4-Cl—Ph) a1 H 4-OiPr a25 H 4-SiMe₄ a35 H 4-(4-Cl—Ph) a2 H 4-OiPr a35 H 4-SiMe₄ a25 H 4-(4-F—Ph) a4 H 4-OiPr a25 H 4-CH₂OEt a35 H 4-(4-F—Ph) a23 H 4-OiPr a35 H 4-CH₂OEt a25 H 4-OPh a25 H 4-OiPr a25 H 4-CH₂Set a35 H 4-OPh a26 H 4-OiPr a35 H 4-CH₂Set a1 H 2-Cl a35 H 4-OiPr a25 H 4-COMe a2 H 2-Cl a1 H 4-OtBu a35 H 4-COMe a4 H 2-Cl a2 H 4-OtBu a25 H 4-CotBu a23 H 2-Cl a4 H 4-OtBu a35 H 4-CotBu a25 H 2-Cl a23 H 4-OtBu a25 H 4-CO₂Me a26 H 2-Cl a25 H 4-OtBu a35 H 4-CO₂Me a35 H 2-Cl a26 H 4-OtBu a25 H 4-CO₂tBu al H 2,4-F₂ a35 H 4-OtBu a35 H 4-CO₂tBu a2 H 2,4-F₂ a1 H 4-OCF₃ a25 H 4-CH₂Ph a4 H 2,4-F₂ a2 H 4-OCF₃ a35 H 4-CH₂Ph a23 H 2,4-F₂ a4 H 4-OCF₃ a25 H 4-OCH₂Ph a25 H 2,4-F₂ a23 H 4-OCF₃ a35 H 4-OCH₂Ph a26 H 2,4-F₂ a25 H 4-OCF₃ a25 H 4-(2-thienyl) a35 H 2,4-F₂ a2 H 2,6-F₂ a25 H 2,3,4,5,6-F₅ a8 H 3-F a4 H 2,6-F₂ a26 H 2,3,4,5,6-F₅ a9 H 3-F a23 H 2,6-F₂ a35 H 2,3,4,5,6-F₅ a10 H 3-F a25 H 2,6-F₂ a1 H 2,3,4,5,6-Cl₅ a11 H 3-F a26 H 2,6-F₂ a2 H 2,3,4,5,6-Cl₅ a12 H 3-F a35 H 2,6-F₂ a4 H 2,3,4,5,6-Cl₅ a13 H 3-F a1 H 2,4-Cl₂ a23 H 2,3,4,5,6-Cl₅ a14 H 3-F a2 H 2,4-Cl₂ a25 H 2,3,4,5,6-Cl₅ a15 H 3-F a4 H 2,4-Cl₂ a26 H 2,3,4,5,6-Cl₅ a16 H 3-F a23 H 2,4-Cl₂ a35 H 2,3,4,5,6-Cl₅ a17 H 3-F a25 H 2,4-Cl₂ a1 H 3-NO₂ a18 H 3-F a26 H 2,4-Cl₂ a2 H 3-NO₂ a19 H 3-F a35 H 2,4-Cl₂ a4 H 3-NO₂ a20 H 3-F a1 H 2,6-Cl₂ a23 H 3-NO₂ a21 H 3-F a2 H 2,6-Cl₂ a25 H 3-NO₂ a22 H 3-F a4 H 2,6-Cl₂ a26 H 3-NO₂ a23 H 3-F a23 H 2,6-Cl₂ a35 H 3-NO₂ a24 H 3-F a25 H 2,6-Cl₂ a1 H 3-CN a25 H 3-F a26 H 2,6-Cl₂ a2 H 3-CN a26 H 3-F a35 H 2,6-Cl₂ a4 H 3-CN a27 H 3-F a1 H 2,4,6-Cl₃ a23 H 3-CN a28 H 3-F a2 H 2,4,6-Cl₃ a25 H 3-CN a29 H 3-F a4 H 2,4,6-Cl₃ a26 H 3-CN a30 H 3-F a23 H 2,4,6-Cl₃ a35 H 3-CN a31 H 3-F a25 H 2,4,6-Cl₃ a1 H 3-F a32 H 3-F a26 H 2,4,6-Cl₃ a2 H 3-F a33 H 3-F a35 H 2,4,6-Cl₃ a3 H 3-F a34 H 3-F a1 H 2,3,4,5,6-F₅ a4 H 3-F a35 H 3-F a2 H 2,3,4,5,6-F₅ a5 H 3-F a36 H 3-F a4 H 2,3,4,5,6-F₅ a6 H 3-F a37 H 3-F a23 H 2,3,4,5,6-F₅ a7 H 3-F a38 H 3-F a39 H 3-F a11 H 3-Cl a42 H 3-Cl a40 H 3-F a12 H 3-Cl a43 H 3-Cl a41 H 3-F a13 H 3-Cl a44 H 3-Cl a42 H 3-F a14 H 3-Cl a45 H 3-Cl a43 H 3-F a15 H 3-Cl a46 H 3-Cl a44 H 3-F a16 H 3-Cl a47 H 3-Cl a45 H 3-F a17 H 3-Cl a48 H 3-Cl a46 H 3-F a18 H 3-Cl a49 H 3-Cl a47 H 3-F a19 H 3-Cl a50 H 3-Cl a48 H 3-F a20 H 3-Cl a51 H 3-Cl a49 H 3-F a21 H 3-Cl a52 H 3-Cl a50 H 3-F a22 H 3-Cl a53 H 3-Cl a51 H 3-F a23 H 3-Cl a54 H 3-Cl a52 H 3-F a24 H 3-Cl a55 H 3-Cl a53 H 3-F a25 H 3-Cl a56 H 3-Cl a54 H 3-F a26 H 3-Cl a57 H 3-Cl a55 H 3-F a27 H 3-Cl a58 H 3-Cl a56 H 3-F a28 H 3-Cl a59 H 3-Cl a57 H 3-F a29 H 3-Cl a1 H 3-Br a58 H 3-F a30 H 3-Cl a2 H 3-Br a59 H 3-F a31 H 3-Cl a4 H 3-Br a1 H 3-Cl a32 H 3-Cl a23 H 3-Br a2 H 3-Cl a33 H 3-Cl a25 H 3-Br a3 H 3-Cl a34 H 3-Cl a26 H 3-Br a4 H 3-Cl a35 H 3-Cl a35 H 3-Br a5 H 3-Cl a36 H 3-Cl a1 H 3-I a6 H 3-Cl a37 H 3-Cl a2 H 3-I a7 H 3-Cl a38 H 3-Cl a4 H 3-I a8 H 3-Cl a39 H 3-Cl a23 H 3-I a9 H 3-Cl a40 H 3-Cl a25 H 3-I a10 H 3-Cl a41 H 3-Cl a26 H 3-I a35 H 3-I a4 H 3-cPr a20 H 3-CF₃ a1 H 3-Me a23 H 3-cPr a21 H 3-CF₃ a2 H 3-Me a25 H 3-cPr a22 H 3-CF₃ a4 H 3-Me a26 H 3-cPr a23 H 3-CF₃ a23 H 3-Me a35 H 3-cPr a24 H 3-CF₃ a25 H 3-Me a1 H 3-cHex a25 H 3-CF₃ a26 H 3-Me a2 H 3-cHex a26 H 3-CF₃ a35 H 3-Me a4 H 3-cHex a27 H 3-CF₃ a1 H 3-iPr a23 H 3-cHex a28 H 3-CF₃ a2 H 3-iPr a25 H 3-cHex a29 H 3-CF₃ a4 H 3-iPr a26 H 3-cHex a30 H 3-CF₃ a23 H 3-iPr a35 H 3-cHex a31 H 3-CF₃ a26 H 3-iPr a1 H 3-CF₃ a32 H 3-CF₃ a26 H 3-iPr a2 H 3-CF₃ a33 H 3-CF₃ a35 H 3-iPr a3 H 3-CF₃ a34 H 3-CF₃ al H 3-tBu a4 H 3-CF₃ a35 H 4-CF₃ a2 H 3-tBu a5 H 3-CF₃ a36 H 3-CF₃ a4 H 3-tBu a6 H 3-CF₃ a37 H 3-CF₃ a23 H 3-tBu a7 H 3-CF₃ a38 H 3-CF₃ a25 H 3-tBu a8 H 3-CF₃ a39 H 3-CF₃ a26 H 3-tBu a9 H 3-CF₃ a40 H 4-CF₃ a35 H 3-tBu a10 H 3-CF₃ a41 H 3-CF₃ a1 H 3-nHex a11 H 3-CF₃ a42 H 3-CF₃ a2 H 3-nHex a12 H 3-CF₃ a43 H 3-CF₃ a4 H 3-nHex a13 H 3-CF₃ a44 H 4-CF₃ a23 H 3-nHex a14 H 3-CF₃ a45 H 3-CF₃ a25 H 3-nHex a15 H 3-CF₃ a46 H 3-CF₃ a26 H 3-nHex a16 H 3-CF₃ a47 H 3-CF₃ a35 H 3-nHex a17 H 3-CF₃ a48 H 3-CF₃ a1 H 3-cPr a18 H 3-CF₃ a49 H 3-CF₃ a2 H 3-cPr a19 H 3-CF₃ a50 H 3-CF₃ a51 H 3-CF₃ a2 H 3-OCF₃ a35 H 3-CH₂Ph a52 H 3-CF₃ a4 H 3-OCF₃ a25 r6 3-OCH₂Ph a53 H 3-CF₃ a23 H 3-OCF₃ a35 H 3-OCH₂Ph a54 H 3-CF₃ a25 H 3-OCF₃ a25 H 3-(2-thienyl) a55 H 3-CF₃ a26 H 3-OCF₃ a35 H 3-(2-thienyl) a56 H 3-CF₃ a35 H 3-OCF₃ a25 H 3-(3-thienyl) a57 H 3-CF₃ a25 H 3-Sine a35 H 3-(3-thienyl) a58 H 3-CF₃ a35 H 3-Sine a25 H 3-(2-pyridyl) a59 H 3-CF₃ a25 H 3-SOMe a35 H 3-(2-pyridyl) a1 H 3-OMe a35 H 3-SOMe a25 H 3-(3-pyridyl) a2 H 3-OMe a25 H 3-SO_(2Me) a35 H 3-(3-pyridyl) a4 H 3-OMe a35 H 3-SO_(2Me) a25 H 3-(4-pyridyl) a23 H 3-OMe a25 H 3-NHMe a35 H 3-(4-pyridyl) a25 H 3-OMe a35 H 3-NHMe a25 H 3-Ph a26 H 3-OMe a25 H 3-NMe₂ a35 H 3-Ph a35 H 3-OMe a35 H 3-NMe₂ a25 H 3-(4-Cl-Ph) a1 H 3-OiPr a25 H 3-SiMe₄ a35 H 3-(4-Cl-Ph) a2 H 3-OiPr a35 H 3-SiMe₄ a25 H 3-(4-F-Ph) a4 H 3-OiPr a25 H 3-CH₂OEt a35 H 3-(4-F-Ph) a23 H 3-OiPr a35 H 3-CH₂OEt a25 H 3-OPh a25 H 3-OiPr a25 H 3-CH₂Set a35 H 3-OPh a26 H 3-OiPr a35 H 3-CH₂Set a1 H 3,5-Cl₂ a35 H 3-OiPr a25 H 3-COMe a2 H 3,5-Cl₂ a1 H 3-OtBu a35 H 3-COMe a3 H 3,5-Cl₂ a2 H 3-OtBu a25 H 3-CotBu a4 H 3,5-Cl₂ a4 H 3-OtBu a35 H 3-CotBu a5 H 3,5-Cl₂ a23 H 3-OtBu a25 H 3-CO₂Me a6 H 3,5-Cl₂ a25 H 3-OtBu a35 H 3-CO₂Me a7 H 3,5-Cl₂ a26 H 3-OtBu a25 H 3-CO₂tBu a8 H 3,5-Cl₂ a35 H 3-OtBu a35 H 3-CO₂tBu a9 H 3,5-Cl₂ a1 H 3-OCF₃ a25 H 3-CH₂Ph a10 H 3,5-Cl₂ a11 H 3,5-Cl₂ a42 H 3,5-Cl₂ a14 H 3,5-F₂ a12 H 3,5-Cl₂ a43 H 3,5-Cl₂ a15 H 3,5-F₂ a13 H 3,5-Cl₂ a44 H 3,5-Cl₂ a16 H 3,5-F₂ a14 H 3,5-Cl₂ a45 H 3,5-Cl₂ a17 H 3,5-F₂ a15 H 3,5-Cl₂ a46 H 3,5-Cl₂ a18 H 3,5-F₂ a16 H 3,5-Cl₂ a47 H 3,5-Cl₂ a19 H 3,5-F₂ a17 H 3,5-Cl₂ a48 H 3,5-Cl₂ a20 H 3,5-F₂ a18 H 3,5-Cl₂ a49 H 3,5-Cl₂ a21 H 3,5-F₂ a19 H 3,5-Cl₂ a50 H 3,5-Cl₂ a22 H 3,5-F₂ a20 H 3,5-Cl₂ a51 H 3,5-Cl₂ a23 H 3,5-F₂ a21 H 3,5-Cl₂ a52 H 3,5-Cl₂ a24 H 3,5-F₂ a22 H 3,5-Cl₂ a53 H 3,5-Cl₂ a25 H 3,5-F₂ a23 H 3,5-Cl₂ a54 H 3,5-Cl₂ a26 H 3,5-F₂ a24 H 3,5-Cl₂ a55 H 3,5-Cl₂ a27 H 3,5-F₂ a25 H 3,5-Cl₂ a56 H 3,5-Cl₂ a28 H 3,5-F₂ a26 H 3,5-Cl₂ a57 H 3,5-Cl₂ a29 H 3,5-F₂ a27 H 3,5-Cl₂ a58 H 3,5-Cl₂ a30 H 3,5-F₂ a28 H 3,5-Cl₂ a59 H 3,5-Cl₂ a31 H 3,5-F₂ a29 H 3,5-Cl₂ a1 H 3,5-F₂ a32 H 3,5-F₂ a30 H 3,5-Cl₂ a2 H 3,5-F₂ a33 H 3,5-F₂ a31 H 3,5-Cl₂ a3 H 3,5-F₂ a34 H 3,5-F₂ a32 H 3,5-Cl₂ a4 H 3,5-F₂ a35 H 3,5-F₂ a33 H 3,5-Cl₂ a5 H 3,5-F₂ a36 H 3,5-F₂ a34 H 3,5-Cl₂ a6 H 3,5-F₂ a37 H 3,5-F₂ a35 H 3,5-Cl₂ a7 H 3,5-F₂ a38 H 3,S-F₂ a36 H 3,5-Cl₂ a8 H 3,S-F₂ a39 H 3,S-F₂ a37 H 3,5-Cl₂ a9 H 3,5-F₂ a40 H 3,S-F₂ a38 H 3,5-Cl₂ a19 H 3,S-F₂ a41 H 3,S-F₂ a39 H 3,5-Cl₂ a11 H 3,5-F₂ a42 H 3,S-F₂ a40 H 3,5-Cl₂ a12 H 3,5-F₂ a43 H 3,S-F₂ a41 H 3,5-Cl₂ a13 H 3,5-F₂ a44 H 3,5-F₂ a45 H 3,5-F₉ a17 H 3,5-Me₉ a48 H 3,5-Me₉ a46 H 3,5-F₂ a18 H 3,5-Me₂ a49 H 3,5-Me₂ a47 H 3,5-F₂ a19 H 3,5-Me₂ a50 H 3,5-Me₂ a48 H 3,5-F₂ a20 H 3,5-Me₂ a51 H 3,5-Me₂ a49 H 3,5-F₂ a21 H 3,5-Me₂ a52 H 3,5-Me₂ a50 H 3,5-F₂ a22 H 3,5-Me₂ a53 H 3,5-Me₂ a51 H 3,5-F₂ a23 H 3,5-Me₂ a54 H 3,5-Me₂ a52 H 3,5-F₂ a24 H 3,5-Me₂ aSS H 3,5-Me₂ a53 H 3,5-F₂ a25 H 3,5-Me₂ a56 H 3,5-Me₂ a54 H 3,5-F₂ a26 H 3,5-Me₂ a57 H 3,5-Me₂ a55 H 3,5-F₂ a27 H 3,5-Me₂ a58 H 3,5-Me₂ a56 H 3,5-F₂ a28 H 3,5-Me₂ a59 H 3,5-Me₂ a57 H 3,5-F₂ a29 H 3,5-Me₂ a60 H — a58 H 3,5-F₂ a30 H 3,5-Me₂ a60 H 4-F a59 H 3,5-F₂ a31 H 3,5-Me₂ a60 H 4-Cl a1 H 3,5-Me₂ a32 H 3,5-Me₂ a60 H 4-iPr a2 H 3,5-Me₂ a33 H 3,5-Me₂ a60 H 4-tBu a3 H 3,5-Me₂ a34 H 3,5-Me₂ a60 H 4-CF₃ a4 H 3,5-Me₂ a35 H 3,5-Me₂ a60 H 3-F a5 H 3,5-Me₂ a36 H 3,5-Me₂ a60 H 3-Cl a6 H 3,5-Me₂ a37 H 3,5-Me₂ a60 H 3-iPr a7 H 3,5-Me₂ a38 H 3,5-Me₂ a60 H 3-tBu a8 H 3,5-Me₂ a39 H 3,5-Me₂ a60 H 3-CF₃ a9 H 3,5-Me₂ a40 H 3,5-Me₂ a60 H 3,5-F₂ a10 H 3,5-Me₂ a41 H 3,5-Me₂ a60 H 3,S-Cl₂ a11 H 3,5-Me₂ a42 H 3,5-Me₂ a60 H 3,5-Me a12 H 3,5-Me₂ a43 H 3,5-Me₂ a60 H 3,5-OMe₂ a13 H 3,5-Me₂ a44 H 3,5-Me₂ a14 H 3,5-Me₂ a45 H 3,5-Me₂ a15 H 3,5-Me₂ a46 H 3,5-Me₂ a16 H 3,5-Me₂ a47 H 3,5-Me₂

TABLE 2

Combinations of R₃, R₄ and Xn of all compounds represented in the above formula 2-1 through 2-15 are exemplified in the following tables. R₃ R₄ Xn R₃ R₄ Xn Me Me 4-F Me cHex 4-Cl Me Et 4-F Me OMe 4-Cl Me nPr 4-F Me OEt 4-Cl Me iPr 4-F Me OnPr 4-Cl Me nBu 4-F Me OiPr 4-Cl Me iBu 4-F Me OnBu 4-Cl Me nPen 4-F Me OiBu 4-Cl Me nHex 4-F Me OnPen 4-Cl Me cPr 4-F Me OnHex 4-Cl Me cBu 4-F Me Ph 4-Cl Me cPen 4-F Me Me 4-tBu Me cHex 4-F Me Et 4-tBu Me OMe 4-F Me nPr 4-tBu Me OEt 4-F Me iPr 4-tBu Me OnPr 4-F Me nBu 4-tBu Me OiPr 4-F Me iBu 4-tBu Me OnBu 4-F Me nPen 4-tBu Me OiBu 4-F Me nHex 4-tBu Me OnPen 4-F Me cPr 4-tBu Me OnHex 4-F Me cBu 4-tBu Me Ph 4-F Me cPen 4-tBu Me Me 4-Cl Me cHex 4-tBu Me Et 4-Cl Me OMe 4-tBu Me nPr 4-Cl Me OEt 4-tBu Me iPr 4-Cl Me OnPr 4-tBu Me nBu 4-Cl Me OiPr 4-tBu Me iBu 4-Cl Me OnBu 4-tBu Me nPen 4-Cl Me OiBu 4-tBu Me nHex 4-Cl Me OnPen 4-tBu Me cPr 4-Cl Me OnHex 4-tBu Me cBu 4-Cl Me Ph 4-tBu Me cPen 4-Cl Me Me 4-CF₃ Me Et 4-CF₃ Me OMe 3-F Me Et 4-CF₃ Me OEt 3-F Me iPr 4-CF₃ Me OnPr 3-F Me nBu 4-CF₃ Me OiPr 3-F Me iBu 4-CF₃ Me OnBu 3-F Me nPen 4-CF₃ Me OiBu 3-F Me nHex 4-CF₃ Me OnPen 3-F Me cPr 4-CF₃ Me OnHex 3-F Me cBu 4-CF₃ Me Ph 3-F Me cPen 4-CF₃ Me Me 3-Cl Me cHex 4-CF₃ Me Et 3-Cl Me OMe 4-CF₃ Me nPr 3-Cl Me OEt 4-CF₃ Me iPr 3-Cl Me OnPr 4-CF₃ Me nBu 3-Cl Me OiPr 4-CF₃ Me iBu 3-Cl Me OnBu 4-CF₃ Me cPen 3-Cl Me OiBu 4-CF₃ Me nHex 3-Cl Me OnPen 4-CF₃ Me cPr 3-Cl Me OnHex 4-CF₃ Me cBu 3-Cl Me Ph 4-CF₃ Me cPen 3-Cl Me Me 3-F Me cHex 3-Cl Me Et 3-F Me OMe 3-Cl Me nPr 3-F Me OEt 3-Cl Me iPr 3-F Me OnPr 3-Cl Me nBu 3-F Me OiPr 3-Cl Me iBu 3-F Me OnBu 3-Cl Me nPen 3-F Me OiBu 3-Cl Me nHex 3-F Me OnPen 3-Cl Me cPr 3-F Me OnHex 3-Cl Me cBu 3-F Me Ph 3-Cl Me cPen 3-F Me Me 3-tBu Me cHex 3-F Me Et 3-tBu Me nPr 3-tBu Me OEt 3,5-F₂ Me iPr 3-tBu Me OnPr 3,5-F₂ Me nBu 3-tBu Me OiPr 3,5-F₂ Me iBu 3-tBu Me OnBu 3,5-F₂ Me nPen 3-tBu Me OiBu 3,5-F₂ Me nHex 3-tBu Me OnPen 3,5-F₂ Me cPr 3-tBu Me OnHex 3,5-F₂ Me cBu 3-tBu Me Ph 3,5-F₂ Me cPen 3-tBu Me Me 3,5-Cl₂ Me cHex 3-tBu Me Et 3,5-Cl₂ Me OMe 3-tBu Me nPr 3,5-Cl₂ Me OEt 3-tBu Me iPr 3,5-Cl₂ Me OnPr 3-tBu Me nBu 3,5-Cl₂ Me OiPr 3-tBu Me iBu 3,5-Cl₂ Me OnBu 3-tBu Me nPen 3,5-Cl₂ Me OiBu 3-tBu Me nHex 3,5-Cl₂ Me OnPen 3-tBu Me cPr 3,5-Cl₂ Me OnHex 3-tBu Me cBu 3,5-Cl₂ Me Ph 3-tBu Me cPen 3,5-Cl₂ Me Me 3,5-F₂ Me cHex 3,5-Cl₂ Me Et 3,5-F₂ Me OMe 3,5-Cl₂ Me nPr 3,5-F₂ Me OEt 3,5-Cl₂ Me iPr 3,5-F₂ Me OnPr 3,5-Cl₂ Me nBu 3,5-F₂ Me OiPr 3,5-Cl₂ Me iBu 3,5-F₂ Me OnBu 3,5-Cl₂ Me nPen 3,5-F₂ Me OiBu 3,5-Cl₂ Me nHex 3,5-F₂ Me OnPen 3,5-Cl₂ Me cPr 3,5-F₂ Me OnHex 3,5-Cl₂ Me cBu 3,5-F₂ Me Ph 3,5-Cl₂ Me cPen 3,5-F₂ Me Me 3,5-Cl₂ Me cHex 3,5-F₂ Me Et 3,5-Cl₂ Me OMe 3,5-F₂ Me nPr 3,5-Cl₂ Me iPr 3,5-Cl₂ Me OnPr 3,5-Me₂ Me nBu 3,5-Cl₂ Me OiPr 3,5-Me₂ Me iBu 3,5-Cl₂ Me OnBu 3,5-Me₂ Me nPen 3,5-Cl₂ Me OiBu 3,5-Me₂ Me nHex 3,5-Cl₂ Me OnPen 3,5-Me₂ Me cPr 3,5-Cl₂ Me OnHex 3,5-Me₂ Me cBu 3,5-Cl₂ Me Ph 3,5-Me₂ Me cPen 3,5-Cl₂ Et nPr 4-F Me cHex 3,5-Cl₂ Et tBu 4-F Me OMe 3,5-Cl₂ Et cPr 4-F Me OEt 3,5-Cl₂ Et OEt 4-F Me OnPr 3,5-Cl₂ Et nPr 4-Cl Me OiPr 3,5-Cl₂ Et tBu 4-Cl Me OnBu 3,5-Cl₂ Et cPr 4-Cl Me OiBu 3,5-Cl₂ Et OEt 4-Cl Me OnPen 3,5-Cl₂ Et nPr 4-tBu Me OnHex 3,5-Cl₂ Et tBu 4-tBu Me Ph 3,5-Cl₂ Et cPr 4-tBu Me Me 3,5-Me₂ Et OEt 4-tBu Me Et 3,5-Me₂ Et nPr 4-CF₃ Me nPr 3,5-Me₂ Et tBu 4-CF₃ Me iPr 3,5-Me₂ Et cPr 4-CF₃ Me nBu 3,5-Me₂ Et OEt 4-CF₃ Me tBu 3,5-Me₂ Et nPr 3-Cl Me nPen 3,5-Me₂ Et tBu 3-Cl Me nHex 3,5-Me₂ Et cPr 3-Cl Me cPr 3,5-Me₂ Et OEt 3-Cl Me cBu 3,5-Me₂ Et nPr 3-tBu Me cPen 3,5-Me₂ Et tBu 3-tBu Me cHex 3,5-Me₂ Et cPr 3-tBu Me OMe 3,5-Me₂ Et OEt 3-tBu Me OEt 3,5-Me₂ Et nPr 3,5-Cl₂ Et tBu 3,5-Cl₂ nPr tBu 3,5-Cl₂ Et cPr 3,5-Cl₂ nPr cPr 3,5-Cl₂ Et OEt 3,5-Cl₂ nPr OEt 3,5-Cl₂ Et nPr 3,5-Me₂ nPr nPr 3,5-Me₂ Et tBu 3,5-Me₂ nPr tBu 3,5-Me₂ Et cPr 3,5-Me₂ nPr cPr 3,5-Me₂ Et OEt 3,5-Me₂ nPr OEt 3,5-Me₂ nPr nPr 4-F iPr nPr 4-F nPr tBu 4-F iPr tBu 4-F nPr cPr 4-F iPr cPr 4-F nPr OEt 4-F iPr OEt 4-F nPr nPr 4-Cl iPr nPr 4-Cl nPr tBu 4-Cl iPr tBu 4-Cl nPr cPr 4-Cl iPr cPr 4-Cl nPr OEt 4-Cl iPr OEt 4-Cl nPr nPr 4-tBu iPr nPr 4-tBu nPr tBu 4-tBu iPr tBu 4-tBu nPr cPr 4-tBu iPr cPr 4-tBu nPr OEt 4-tBu iPr OEt 4-tBu nPr nPr 4-CF₃ iPr nPr 4-CF₃ nPr tBu 4-CF₃ iPr tBu 4-CF₃ nPr cPr 4-CF₃ iPr cPr 4-CF₃ nPr OEt 4-CF₃ iPr OEt 4-CF₃ nPr nPr 3-Cl iPr nPr 3-Cl nPr tBu 3-Cl iPr tBu 3-Cl nPr cPr 3-Cl iPr cPr 3-Cl nPr OEt 3-Cl iPr OEt 3-Cl nPr nPr 3-tBu iPr nPr 3-tBu nPr tBu 3-tBu iPr tBu 3-tBu nPr cPr 3-tBu iPr cPr 3-tBu nPr OEt 3-tBu iPr OEt 3-tBu nPr nPr 3,5-Cl₂ iPr nPr 3,5-Cl₂ iPr tBu 3,5-Cl₂ nBu tBu 3,5-Cl₂ iPr cPr 3,5-Cl₂ nBu cPr 3,5-Cl₂ iPr OEt 3,5-Cl₂ nBu OEt 3,5-Cl₂ iPr nPr 3,5-Me₂ nBu nPr 3,5-Me₂ iPr tBu 3,5-Me₂ nBu tBu 3,5-Me₂ iPr cPr 3,5-Me₂ nBu cPr 3,5-Me₂ iPr OEt 3,5-Me₂ nBu OEt 3,5-Me₂ nBu nPr 4-F tBu nPr 4-F nBu tBu 4-F tBu tBu 4-F nBu cPr 4-F tBu cPr 4-F nBu OEt 4-F tBu OEt 4-F nBu nPr 4-Cl tBu nPr 4-Cl nBu tBu 4-Cl tBu tBu 4-Cl nBu cPr 4-Cl tBu cPr 4-Cl nBu OEt 4-Cl tBu OEt 4-Cl nBu nPr 4-tBu tBu nPr 4-tBu nBu tBu 4-tBu tBu tBu 4-tBu nBu cPr 4-tBu tBu cPr 4-tBu nBu OEt 4-tBu tBu OEt 4-tBu nBu nPr 4-CF₃ tBu nPr 4-CF₃ nBu tBu 4-CF₃ tBu tBu 4-CF₃ nBu cPr 4-CF₃ tBu cPr 4-CF₃ nBu OEt 4-CF₃ tBu OEt 4-CF₃ nBu nPr 3-Cl tBu nPr 3-Cl nBu tBu 3-Cl tBu tBu 3-Cl nBu cPr 3-Cl tBu cPr 3-Cl nBu OEt 3-Cl tBu OEt 3-Cl nBu nPr 3-tBu tBu nPr 3-tBu nBu tBu 3-tBu tBu tBu 3-tBu nBu cPr 3-tBu tBu cPr 3-tBu nBu OEt 3-tBu tBu OEt 3-tBu nBu nPr 3,5-Cl₂ nPen tBu 4-Cl (Pest Controlling Agent)

The compounds of the present invention are useful as active ingredients for pest controlling agents, particularly as agricultural and horticultural insecticides, acaricides, sanitary pest controlling agents and anti-fouling agents for aqueous adhesive organisms. It is particularly preferable to apply compositions containing the compounds of the present invention as agricultural and horticultural insecticides and acaricides.

The compounds of the present invention can be used in their pure form without adding other ingredients, when they are actually applied as agricultural and horticultural insecticides or acaricides. When applied as agrochemicals, they may be used in forms that general agrochemicals can take, such as wettable powders, granules, dusts, emulsifiable concentrates, water soluble powders, flowable concentrates and flowables.

In order to make solid formulations, vegetable powders such as soybean flour and wheat flour, fine mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophylite and clay: and organic and inorganic compounds such as sodium benzoate, urea and Glauber's salt can be used as additives and carriers. When the purpose is to prepare liquid formulations, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, N,N-dimethylformamide, dimethylsulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oils, vegetable oils, water and the like can be used as solvents.

It is possible to further add surfactant, if required, to make these formulations homogeneous and stable forms. There is no particular restriction on which surfactant can be used. Their examples include nonionic surfactant such as polyoxyethylene-added alkyl ethers, polyoxyethylene-added higher fatty acid esters, polyoxyethylene-added sorbitan higher fatty acid esters and polyoxyethylene-added tristylylphenyl ethers; polyoxyethylene-added alkylphenyl ether sulfates, alkylnaphthalene sulfonates, polycarboxylic acid salts, lignin sulfonates, condensation products of alkylnaphthalene sulfonates with formaldehyde, and copolymers of isobutylene and maleic anhydride.

An amount of the active ingredient in a formulation is preferably 0.01 to 90% by weight, more preferably about 0.05 to 85% by weight. The obtained wettable powders, emulsifiable concentrates, flowable concentrates and flowables are diluted with water to specified concentrations to use as suspensions or emulsions. The dusts and granules are used as they are to directly spray on plants or soil.

It goes without saying that the compounds of the present invention are sufficiently effective by themselves. They can be used, however, by mixing with one or more of various fungicides, insecticides, acaricides or synergists.

Representative examples of said fungicides, insecticides, acaricides and plant growth regulators that can be used to mix with the compounds of the present invention are recited in the following:

Fungicides:

Captan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb, Polycarbamate, Chlorothalonil, Quintozene, Captafol, Iprodione, Procymidone, Vinclozolin, Fluorimide, Cymoxanil, Mepronil, Flutolanil, Pencycuron, Oxycarboxine, Fosetyl aluminium, Propamocarb, Triadimefon, Triadimenol, Propiconazole, Diclobutrazol, Bitertanol, Hexaconazol, Microbutanil, Flusilazole, Etaconazole, Fluotrimazole, Flutriafen, Penconazole, Diniconazole, Cyproconazole, Fenarimol, Triflumizole, Prochloraz, Imazalyl, Pefurazoate, Tridemorph, Fenpropimorph, Triforine, Buthiobate, Pyrifenox, Anilazine, Polyoxins, Metalaxyl, Oxadixyl, Furalaxyl, Isoprothiolane, Probenazole, Pyrrolenitrine, Blastocidin-S, Kasugamycin, Balidamycin, Dihydrostreptomycin sulfate, Benomyl, Carbendazim, Thiophanate methyl, Hymexazol, Basic copper chloride, Basic copper sulfate, Fentin acetate,

Triphenyltin hydroxide, Diethofencarb, Metasulfocarb, Quinomethionate, Binapacryl, Lecithin, Sodium hydrogencarbonate, Dithianone, Dinocap, Fenaminosulf, Diclomezine, Guazatine, Dodine, IBP, Edifenphos, Mepanipyrim, Ferimzone, Trichlamide, Metasulfocarb, Fluazinam, Ethoquinolac, Dimetomorph, Pyroquilon, Tecloftalam, Fthalide, Fenazine oxide, Thiabedazole, Tricyclazole, Vinclozolin, Cymoxanil, Cyclobutanil, Guaztine, Propamocarb hydrochloride, Oxolinic acid:

Insecticide/Acaricide

Organophosphorous and Carbamate Insecticides:

Fenthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Bamidothion, Fenthoate, Dimethoate, Formothion, Malathon, Trichlorfon, Thiometon, Phosmet, Dichlorvos, Acephate, EPBP, Methyl parathion, Oxydimeton methyl, Ethion, Salithion, Cyanophos, Isoxathione, Pyridafenthion, Phosalone, Methidathion, Sulprofos, Chlorfevinphos, Tetrachlorvinphos, Dimethylvinphos, Propaphos, Isofenphos, Ethyl thiometon, Profenophos, Pyraclofos, Monocrotophos, Azinphos methyl, Aldicarb, Methomyl, Dithiocarb, Carbofuran, Carbosulfan, Benfuracarb, Furathiocarb, Propoxur, BPMC, MTMC, MIPC, carbaryl, Pyrimicarb, Ethiofencarb, Fenoxycarb, cartap, thiocyclam, bensultap, etc.

Pyrethroid insecticides:

Permethrin, Cypermethrin, Deltamethrin, Fenvalerate, Fenpropathrin, Pyrethrin, Allethrin, Tetramethrin, Resmethrin, Dimethrin, Propathrin, Fenothrin, Prothrin, Fluvarinate, Cyfluthrin, Cyhalothrin, Flucythrinate, Ethofenprox, Cycloprothrin, Tralomethrin, Silafluofen, Brofenprox, Acrinathrin, etc.

Benzoyl Urea and other Insecticides:

Diflubenzuron, Chlorfluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Fulfenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Methoprene, Benzoepin, Diafenthiuron, Imidacloprid, Fipronyl, Nicotin sulfate, Rotenone, Metaldehyde, Machine oil, Microbial insecticides such as BT and insect-pathogenic viruses, etc.

Nematicides:

Fenamiphos, Fosthiazate, etc.

Acaricides:

Chlorbenzilate, Fenisobromolate, Dicofol, Amitraz, BPPS, Benzomate, Hexythiazox, Fenbutatin oxide, Polynactin, Quinomethionate, CPCBS, Tetradifon, Avermectin, Milbemectin, Clofentezin, Cyhexatin, Pyridaben, Fenproxymate, Tebufenpyrad, Pyrimidifen, Fenothiocarb, Dienochlor, etc.

Plant Growth Regulators:

Gibberellins (e.g., Gibberellin A3, Gibberellin A4, Gibberellin A7), IAA, NAA, etc.

The compound of the present invention can be used to control agricultural pests, sanitary insect pests, stored grain insect pests, cloth insect pests, house insect pests and the like, and have activities of killing adults, nymphs, larvae and eggs. Their representative examples are shown in the following.

Examples of Lepidopterous pest insects include cotton leafworm, cabbage armyworm, black cutworm, common cabbageworm, cabbage looper, diamond-back moth, smaller tea tortrix, tea leaf roller, peach fruit moth, oriental fruit moth, citrus leaf miner, tea leaf roller, apple leaf miner, gypsy moth, tea tussock moth, rice stem borer, grass leaf roller, European corn borer, fall webworm, almond moth, Heliothis sp., Helicoverpa sp., Agrotis sp., casemaking clothes moth, codling moth and cotton bollworm.

Examples of Hemipterous pest insects include green peach aphis, cotton aphid, turnip aphid, grain aphid, bean bug, common green stink bug, arrowhead scale, mulberry mealy scale, greenhouse whitefly, tobacco whitefly, pear psylla, Japanese pear lace bug, brown planthopper, small brown planthopper, white-backed planthopper and green rice leafhopper.

Examples of Coleopterous pest insects include striped flea beetle, cucurbit leaf beetle, Colorado potato beetle, rice water weevil, rice weevil, adzuki bean weevil, Japanese beetle, soybean beetle, Diabrotica sp., cigarette beetle, powder post beetle, pine sawyer, white-spotted longicom beetle, Agriotis sp., 28-spotted lady beetle, rust-red flour beetle and cotton boll weevil.

Examples of Dipterous pest insects include housefly, Calliphora lata, Boettcherisca peregrina, cucurbit fruit fly, citrus fruit fly, seed maggot, rice leaf miner, yellow drosophila, Stomoxys calcitrans, Culex tritaeniarhynchus, Aedes aegypti and Anopheles hyrcanus.

Examples of Thysanopterous pest insects include Thrips palmi and tea thrips.

Examples of Hymenopterous pest insects include Monomorium pharaonis, yellow hamet and cabbage sawfly.

Examples of Orhtopterous pest insects include grasshopper, German cockroach, American cockroach and Japanese cockroach.

Examples of Isopterous pest insects include Formosan subterranean termite and Reticulitermes speratus Kolbe.

Examples of Aphanipterous pest insects include human flea.

Examples of Anoplurous pest insects include human louse.

Examples of mites include two-spotted spider mite, Kanzawa spider mite, citrus red mite, European red mite, citrus rust mite, apple rust mite, Tarsonemus sp., Brevipalpus sp., Eotetranychus sp., Robin bulb mite, common grain mite, Desmatophagoides farinae, Boophilus microplus and Haemaphysallis bispinosa.

Examples of plant-parasitic nematodes include southern root-knot nematode, root lesion nematode, soybean cyst nematode, rice white-tip nematode, and pine wood nematode.

Among the pest insects as recited above, Lepidopterous pest insects, Hemipterous pest insects, Coleopterous pest insects, Thysanopterous pest insects, and mites are preferable targets for the compounds of the present invention, and particularly, Lepidopterous and Coleopterous pest insects and mites are the most preferable targets.

In recent times, various pest insects, such as diamond-back moths, planthoppers, leafhoppers, aphids, phytophagous mites have developed resistance against organophosphorous insecticides, carbamate insecticides and acaricides. Therefore, the foresaid insecticides and acaricides have lost their efficacy against pest insects and mites that have developed resistance against them. Accordingly, there has been a desire for chemicals that are effective on pest insects and mites of the resistance strains. The compounds of the present invention are chemicals having excellent insecticidal and acaricidal effects on pest insects resistant to organophosphorous pesticides, carbamate insecticides or pyrethroid pesticides and mites resistant to acaricides, as well as those of sensitive strains.

The compounds of the present invention induce very slight phytotoxicity on plants, have low toxicity on fishes and warm-blood animals, and are highly safe.

Further, the compounds of the present invention can be used also as an anti-fouling agent that prevents aqueous adhesive organisms from adhering to structures situated in water such as the bottom of a vessel, fishing nets and the like.

BEST MODES TO IMPLEMENT THE INVENTION

The present invention is further described in detail with reference to the following Examples.

EXAMPLE 1

Preparation of α-(4-tert-butyl-N-methylanilino)-β-hydroxy-(2-trifluoromethylphenyl)acrylonitrile (Compound No. 3—3)

To a suspension of 1.16 g of 2-trifluoromethylbenzoic acid and 1.13 g of potassium hydroxide (oily state) in 30 ml of tetrahydrofuran (THF) was added dropwise 0.85 g of 4-tert-butyl-N-cyanomethyl-N-methylaniline in THF solution under cooling in an ice-bath, and the mixture obtained was stirred for 3 hours at room temperature. To the reacted solution was added saturated aqueous solution of ammonium chloride, and the solution was then extracted with diethyl ether. The organic layer was washed with water and was then evaporated under diminished pressure. The mixture obtained was purified by chromatography on silica-gel column (ethyl acetate/n-hexane=1/4, as an eluent) to give 1.02 g of the title compound. Yield: 65%. Melting point: 170-171° C.

EXAMPLE 2

Preparation of β-(5-chloro-1-methyl-3-trifluoromethylpyrazole-4-yl)-α-(4-chlorophenoxy)-β-hydroxyacrylonitrile (Compound No. 3-8)

In 4 ml of THF was dissolved 0.4 g of 4-chlorophenoxyacetonitrile. To the solution obtained were added 3 ml of 1.6M n-butyl lithium and 0.59 g of 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic chloride, successively, at −78° C. and then left to stand overnight at room temperature. The reaction mixture was poured into ice-water, acidified with conc. hydrochloric acid, and then, extracted with ethyl acetate. The organic layer was evaporated under diminished pressure to give 0.62 g of the title compound. Yield: 69%. Melting point: 126-128° C.

EXAMPLE 3

Preparation of β-(5-chloro-1-methyl-3-trifluoromethylpyrazole-4-yl)-α-(4-chlorophenoxy)-β-pivaloyloxyacrylonitrile (Compound No. 3-9)

In 5 ml of acetonitrile was dissolved 0.30 g of β-(5-chloro-1-methyl-3-trifluoromethylpyrazole-4-yl)-α-(4-chlorophenoxy)-β-hydroxyacrylonitrile. To the solution obtained were added 0.10 g of triethylamine and 0.12 g of pivaloyl chloride, successively, at 0° C. The mixture obtained was stirred for 5 hours at room temperature. The insoluble material was filtered off, and the filtrate was evaporated under diminished pressure. The mixture obtained was purified by chromatography on silica-gel column (ethyl acetate/n-hexane=3/1, as an eluent) to give 0.28 g of the title compound. Yield: 72%. Refractive index: n_(D) ^(25.1) 1.5058

The compounds prepared in such a way as described above as well as the compounds disclosed in the above Examples were shown in Tables 3 and 4. Similarly, the NMR data of oily substances and others are shown in Table 5.

TABLE 3

Compound Physical No. A R Xn Y Constant (m.p.) 3-1  a1 H — NMe [102-104] 3-2  a1 H 4-Cl NMe [160-162] 3-3  a1 H 4-tBu NMe [170-171] 3-4  a23 H — NMe [117] 3-5  a25 H — NMe [151] 3-6  a1 H 4-Cl O NMR 3-7  a1 r6 4-Cl O n_(D) ^(25.1)1.5157 3-8  a25 H 4-Cl O [126-128] 3-9  a25 r6 4-Cl O n_(D) ^(25.1)1.5058 3-10 a1 H 4-Cl S NMR 3-11 a1 r6 4-Cl S n_(D) ^(24.5)1.5333 3-12 a25 H 4-Cl S NMR 3-13 a25 r6 4-Cl S n_(D) ^(25.1)1.5369 3-14 a25 H — SO₂ [161-163] 3-15 a25 r6 — SO₂ NMR (b) 3-16 a25 H — O NMR 3-17 a25 r6 — O n_(D) ^(25.1)1.5100 3-18 a25 r6 — O n_(D) ^(25.2)1.4980 (c) 3-19 a25 H 2-Cl O NMR 3-20 a25 r6 2-Cl O [121-122] 3-21 a25 H 3-Cl O NMR 3-22 a25 r6 3-Cl O n_(D) ^(23.9)1.5081 3-23 a25 r22 4-Cl O n_(D) ^(22.9)1.5230 3-24 a25 r24 4-Cl O n_(D) ^(23.0)1.5282 3-25 a25 H 2,6-Cl₂ O NMR 3-26 a25 r6 2,6-Cl₂ O n_(D) ^(22.7)1.5071 3-27 a25 H 3,5-Cl₂ O NMR 3-28 a25 r6 3,5-Cl₂ O n_(D) ^(24.0)1.5151 3-29 a25 H 4-F O [134-136] 3-30 a25 r6 4-F O n_(D) ^(23.2)1.4863 3-31 a25 r22 4-F O n_(D) ^(22.7)1.5248 3-32 a25 H 3-tBu O [228-230] 3-33 a25 r6 3-tBu O n_(D) ^(22.4)1.4900 3-34 a25 r22 3-tBu O n_(D) ^(22.4)1.5063 3-35 a25 H 4-tBu O [115-118] 3-36 a25 r6 4-tBu O n_(D) ^(22.4)1.4946 3-37 a25 r22 4-tBu O n_(D) ^(22.4)1.5250 3-38 a25 H 3,5-Me₂ O [135-136] 3-39 a25 r6 3,5-Me₂ O n_(D) ^(23.3)1.4892 3-40 a25 H 4-CF₃ O [118-119] 3-41 a25 r6 4-CF₃ O n_(D) ^(22.7)1.4719 3-42 a25 r22 4-CF₃ O n_(D) ^(23.0)1.5022 3-43 a29 H 4-CF₃ O NMR 3-44 a29 r6 4-CF₃ O NMR 3-44 a29 r6 4-CF₃ O n_(D) ^(22.6)1.4902 3-45 a35 H 4-CF₃ O NMR 3-46 a35 r6 4-CF₃ O n_(D) ^(22.6)1.4890 3-47 a60 H 4-CF₃ O NMR 3-48 a60 r6 4-CF₃ O n_(D) ^(22.6)1.5167 3-49 a25 r49 4-CF₃ O n_(D) ^(22.1)1.4808 3-50 a29 r49 4-CF₃ O n_(D) ^(22.2)1.5104 3-51 a60 H 4-Cl O NMR 3-52 a25 H 4-OPh O NMR 3-53 a25 r6 4-OPh O n_(D) ^(23.8)1.5282 3-54 a25 r6 4-OPh O n_(D) ^(23.8)1.5250 (d) 3-55 a25 H 3-Ph O NMR 3-56 a25 r6 3-Ph O n_(D) ^(22.8)1.5338 3-57 a25 r6 3-Ph O n_(D) ^(22.8)1.5498 (e) 3-58 a25 H 3-Br O NMR 3-59 a25 r6 3-Br O n_(D) ^(22.8)1.5152 3-60 a25 H 3-I O NMR 3-61 a25 r6 3-I O n_(D) ^(24.0)1.4958 3-62 a25 H 3-OPh O NMR 3-63 a25 r6 3-OPh O n_(D) ^(24.1)1.5220 3-64 a25 H 3-iPr O NMR 3-65 a25 r6 3-iPr O n_(D) ^(23.4)1.5008 3-66 a25 r6 3-iPr O n_(D) ^(23.4)1.4920 (f) 3-67 a25 H 3-Me O NMR 3-68 a25 r6 3-Me O NMR 3-69 a25 H 2,3-Me₂ O NMR 3-70 a25 r6 2,3-Me₂ O n_(D) ^(24.0)1.4843 3-71 a25 H 3-OMe O NMR 3-72 a25 r6 3-OMe O n_(D) ^(23.9)1.4885 3-73 a36 H 4-tBu O NMR 3-74 a25 H 3,4-Me₂ O NMR 3-75 a25 H 4-CN O NMR 3-76 a25 H 4-CN O NMR *[ ]: melting point ° C., n_(D): refractive index NMR: ¹H-NMR data are shown on table 5. (b): mixture of isomers Others are an isomer. (c): isomer of 3-17 (d): an isomer of 3-52, (e): an isomer of 3-56, (f): an isomer of 3-65

TABLE 4

Compound Physical No. A R₁ R₂ Xn Constant (m.p.) 4-1  a25 Me nPr 4-F n_(D) ^(23.9)1.4892 4-2  a25 Me tBu 4-F n_(D) ^(23.9)1.4480 4-3  a25 Me cPr 4-F n_(D) ^(24.0)1.4958 4-4  a25 Me OEt 4-F n_(D) ^(24.0)1.4869 4-5  a25 Me nPr 2-Cl n_(D) ^(22.5)1.5130 4-6  a25 Me nPr 2-Cl n_(D) ^(22.6)1.5081 (g) 4-7  a25 Me nPr 3-Cl n_(D) ^(24.0)1.5117 4-8  a25 Me nPr 4-Cl n_(D) ^(25.3)1.5042 4-9  a25 Me tBu 4-Cl n_(D) ^(25.3)1.4942 4-10 a25 Me cPr 4-Cl n_(D) ^(25.4)1.5115 4-11 a25 Me OEt 4-Cl n_(D) ^(25.4)1.4994 4-12 a60 Me nPr 4-Cl n_(D) ^(23.0)1.5531 4-13 a25 Me nPr 2,6-Cl₂ n_(D) ^(22.5)1.5152 4-14 a25 Me nPr 3,5-Cl₂ n_(D) ^(22.3)1.5049 4-15 a25 Me nPr 4-tBu n_(D) ^(22.3)1.4817 4-16 a25 Me tBu 4-tBu n_(D) ^(22.3)1.4834 4-17 a25 Me cPr 4-tBu n_(D) ^(22.3)1.4978 4-18 a25 Me OEt 4-tBu n_(D) ^(22.3)1.4875 4-19 a25 Me nPr 3,5-Me₂ n_(D) ^(23.0)1.5011 4-20 a25 Me nPr — n_(D) ^(25.1)1.4988 4-21 a25 Me nPr 4-CF₃ n_(D) ^(22.3)1.4775 4-22 a60 Me nPr 4-CF₃ n_(D) ^(25.0)1.5178 4-23 a25 Me nPr 4-OPh n_(D) ^(21.7)1.5300 4-24 a25 Me nPr 3-Ph n_(D) ^(23.5)1.5411 4-25 a25 Me nPr 3-Ph n_(D) ^(23.5)1.5365 (h) 4-26 a25 Me nPr 3-Br n_(D) ^(22.7)1.5140 4-27 a25 Me nPr 3-I n_(D) ^(23.5)1.5030 4-28 a25 Me nPr 3-OPh n_(D) ^(23.5)1.5242 4-29 a25 Me nPr 3-iPr n_(D) ^(23.2)1.4952 4-30 a25 Me nPr 3-Me n_(D) ^(23.6)1.5000 4-31 a25 Me nPr 2,3-Me₂ n_(D) ^(24.0)1.4773 4-32 a25 Me nPr 3-OMe n_(D) ^(23.9)1.4916 4-33 a36 Me nPr 4-tBu n_(D) ^(21.0)1.5136 4-34 a36 Me tBu 4-tBu Viscous oil 4-35 a36 Me cPr 4-tBu n_(D) ^(17.4)1.5329 4-36 a36 Me OEt 4-tBu n_(D) ^(20.7)1.5013 4-37 a25 Me OEt 3-tBu n_(D) ^(22.4)1.4820 4-38 a36 Me nPr 3-tBu n_(D) ^(22.7)1.5177 4-39 a36 Me tBu 3-tBu n_(D) ^(22.4)1.4912 4-40 a36 Me OEt 3-tBu n_(D) ^(20.0)1.5069 4-41 a25 Me nPr 3,4-Me₂ n_(D) ^(22.7)1.5049 4-42 a25 Me tBu 3,4-Me₂ n_(D) ^(22.7)1.5064 4-43 a25 Me tBu 3,4-Me₂ n_(D) ^(22.7)1.5046 (i) 4-44 a25 Me nPr 4-CN n_(D) ^(22.7)1.5141 (g): an isomer of 4-5 (h): an isomer of 4-24, (i): an isomer of 4-42

TABLE 5 NMR data Compound No. ¹H-NMR (CDCl₃) 3-6 7.08 (d, 2H), 7.35 (d, 2H), 7.63-7.89 (m, 5H) 3-10 7.34 (s, 4H), 7.59-7.85 (m, 5H) 3-12 3.98 (s, 3H), 7.28-7.54 (m, 4H) 3-15 2.37 and 2.40 (2s, total 3H), 3.96 and 3.99 (2s, total 3H), 7.36-7.89 (m) and 8.06 (d) (total 5H) (a) 3-16 3.94 (s, 3H), 6.89-7.28 (m, 5H) 3-19 3.98 (s, 3H), 7.12-7.50 (m, 4H) 3-21 3.96 (s, 3H), 6.84-7.18 (m, 4H) 3-25 3.95 (s, 3H), 6.82 (t, 2H), 7.26 (d, 1H) 3-27 3.91 (s, 3H), 6.74 (s, 2H), 7.00 (s, 1H) 3-43 2.38 (s, 3H), 2.48 (s, 3H), 3.82 (s, 3H), 7.09 (d, 2H), 7.61 (d, 2H) 3-45 2.22 (s, 3H), 2.25 (s, 3H), 4.11 (s, 3H), 7.14 (d, 2H), 7.67 (d, 2H) 3-47 2.74 (s, 3H), 2.79 (s, 3H), 7.17 (d, 2H), 7.68 (d, 2H) 3-51 2.74 (s, 3H), 2.79 (s, 3H), 7.03 (d, 2H), 7.43 (d, 2H) 3-52 3.98 (s, 3H), 6.98-7.38 (m, 9H) 3-55 3.98 (s, 3H), 6.96-7.63 (m, 9H) 3-58 3.98 (s, 3H), 6.99-7.42 (m, 4H) 3-60 3.98 (s, 3H), 7.06-7.45 (m, 4H) 3-62 3.95 (s, 3H), 6.65-7.44 (m, 9H) 3-64 1.23 (d, 3H), 2.82-2.98 (m, 1H), 3.95 (s, 3H), 6.75-7.06 (m, 3H), 7.25- 3-67 2.35 (s, 3H), 3.95 (s, 3H), 6.80-7.01 (m, 3H), 7.22-7.30 (m, 1H) 3-69 2.18 (s, 3H), 2.30 (s, 3H), 3.95 (s, 3H), 6.75-7.15 (m, 3H) 3-71 4.75 (s, 3H), 3.95 (s, 3H), 6.52-6.72 (m, 3H), 7.21-7.30 (m, 1H) 3-74 1.28 (s, 9H), 2.23 (s, 3H), 3.83 (s, 3H), 7.03 (d, 2H), 7.34 (d. 2H) 3-75 2.23 (s, 3H), 2.28 (2, 3H), 3.98 (s, 3H), 6.53-7.15 (m, 3H) 3-76 3.99 (s, 3H), 6.90 (d, 2H), 7.20 (d, 2H) 3-77 1.11 (s, 9H), 4.00 (s, 3H), 7.20 (d, 2H), 7.72 (d, 2H) 4-34 1.11 (s, 9H), 1.32 (s, 9H), 1.48 (d, 3H), 2.28 (s, 3H), 3.94 (s, 3H), 6.01-6.13 (m, 1H) 7.03 (d, 2H), 7.39 (d, 2H) (a): data of mixture of isomers

A few examples of compositions of the present invention are described below. Additives and addition ratios are not limited to those in the examples, and can be changed in a wide range. The “parts” used in the formulation examples are parts by weight.

EXAMPLE 4 Wettable Powder

A compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkylnaphthalene sulfonate 3 parts

The above compounds were mixed uniformly and pulverized finely to give a wettable powder containing 40% of the active ingredient.

EXAMPLE 5 Emulsifiable Concentrate

A compound of the present invention 30 parts Xylene 33 parts N,N-dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts

The above compounds were mixed and solved to give an emulsifiable concentrate containing 30% of the active ingredient.

EXAMPLE 6 Dust

A compound of the present invention 10 parts Talc 89 parts Polyoxyethylene alkylallyl ether 1 part

The above compounds were mixed uniformly and pulverized finely to give a dust containing 10% of the active ingredient.

EXAMPLE 7 Granules

A compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Sodium dioctylsulfosuccinate 1 part Sodium phosphate 1 part

The above compounds were sufficiently pulverized and mixed. To the obtained mixture was added water, followed by thorough kneading, granulation and drying to give granules containing 5% of the active ingredient.

EXAMPLE 8 Flowable Concentrate

A compound of the present invention 10 parts Sodium lignin sulfonate 4 parts Sodium dodecylbenzenesulfonate 1 part Xanthane gum 0.2 parts Water 84.8 parts

The above compounds were mixed and wet pulverized until the granule size became smaller than 1 μm to give a flowable concentrate containing 10% of the active ingredient.

Availability in Industry

Examples are shown below that formulations containing the compounds of the present invention, which were prepared according to such ways as described above, were applied as an insecticidal/acaricidal agent for controlling pest insects and mites.

TEST EXAMPLE 1 Efficacy on Cotton Aphids

Adult cotton aphids were put onto leaves of cucumbers at the stage of 10 days after germination, planted in a pot with a diameter of c.a. 10 cm. On the following day, all of the adult aphids on the leaves were removed to thereby obtain cucumber leaves infested with the 1st instar nymphs. An emulsifiable concentrate formulation prepared according to the Example 8 was diluted with water so that the concentration of the compound became 125 ppm, followed by spraying thereof over the aphids. Then, the aphids subjected to the spraying were placed in a thermostatic chamber where temperature is maintained at 25° C. and relative humidity was maintained at 65%. Five days later, the aphids were checked to determine their percentage mortality. The test was carried out in duplicate.

As a result of the tests, the compounds listed below revealed 100% percentage mortality.

Note that pyrimicarb provided as a check product has showed a percentage mortality of 9%.

Compound Nos. 3-7, 3-9, 3-17, 3-20, 3-22, 3-23, 3-24, 3-28, 3-30, 3-31, 3-36, 3-41, 3-42, 3-44, 3-46, 3-48, 3-49, 3-56, 3-59, 3-61, 4-5, 4-6, 4-7, 4-8, 4-10, 4-11, 4-14, 4-21, 4-22, 4-24, 4-26

TEST EXAMPLE 2 Effects on Two-Spotted Spider Mite

Fifteen adult females of two-spotted spider mite having acquired resistance to organophosphorous insecticides were put onto the first true leaves of a French bean at the stage of 7-10 days after the germination, planted in a pot with a diameter of c.a. 10 cm. A wettable powder formulation prepared according to the Example 4 was diluted with water so that the concentration of the compound became 125 ppm, followed by spraying thereof over the mites. Then, the mites on the plants were placed in a thermostatic room wherein temperature is maintained at 25° C. and relative humidity is maintained at 65%. Three days later, the mites were checked for their percentage mortality. The test was carried out in duplicate.

As a result of the tests, it was noted that the compounds listed below revealed 100% percentage mortality on the third day after the spraying.

Note that chlordimeform used as a check product has showed a percentage mortality of 13%.

Compound Nos. 3-7, 3-8, 3-9, 3-13, 3-17, 3-18, 3-20, 3-22, 3-23, 3-24, 3-26, 3-28, 3-29, 3-30, 3-31, 3-33, 3-34, 3-36, 3-37, 3-38, 3-39, 3-40, 3-41, 3-42, 3-44, 3-46, 3-48, 3-49, 3-50, 3-54, 3-56, 3-57, 3-59, 3-61, 3-63, 3-65, 3-66, 3-68, 3-70, 3-72, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 4-31, 4-32

TEST EXAMPLE 3 Effects on Citrus Red Mite

Eight adult females of susceptible Citrus red mite were inoculated on the surface of Citrus leaf placed in a glass Petridish. A wettable powder formulation prepared according to the Example 4 was diluted with water so that the concentration of the compound became 125 ppm. The solution was sprayed on the mites using a rotary spraying tower up to the fixed volume. Then, the mites on the leaf were placed in the thermostatic room wherein temperature is maintained at 25° C. and relative humidity is maintained at 65%. Three days later, the mites were checked for their percentage mortality. The test was carried out in duplicate.

As a result of the tests, it was noted that the compounds listed below revealed 100% percentage mortality on the third day after the spraying.

Note that chlordimeform used as a chek product has showed a percentage mortality of 13%.

Compound Nos.: 3-7, 3-9, 3-13, 3-17, 3-18, 3-20, 3-22, 3-23, 3-24, 3-26, 3-28, 3-29, 3-30, 3-31, 3-33, 3-34, 3-36, 3-37, 3-39, 3-40, 3-41, 3-42, 3-44, 3-46, 3-48, 3-49, 3-50, 3-54, 3-56, 3-57, 3-59, 3-61, 3-63, 3-65, 3-66, 3-68, 3-70, 3-72, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 4-31, 4-32 

1. Compounds represented by Formula (1);

wherein A is phenyl substituted by W or a heterocyclic group substituted by W; wherein W is nitro, cyano, halogeno, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl, C₁₋₆ alkcoxycarbonyl, phenyl optionally substituted by G₁, or phenoxy optionally substituted by G₁; wherein G¹ is nitro, cyano, halogeno, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl, or C₁₋₆ alkoxycarbonyl; said heteroyclic group is a 5- or 6-membered heterocyclic group that contains at least one heteroatom selected from a group consisting of oxygen, sulfur and nitrogen; when either of said phenyl or said heterocyclic group contains 2 or more substituents W, said W may be same or different from each other; R is hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy C₁₋₆ alkyl, C₁₋₆ alkylcarbonyloxy C₁₋₆ alkyl, C₃₋₆ cycloalkylcarbonyloxy C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyloxy C₁₋₆ alkyl, optionally substituted phenylcarbonyloxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, C₁₋₆ alkylcarbonylthio C₁₋₆ alkyl, C₃₋₆ cycloalkylcarbonylthio C₁₋₆ alkyl, C₁₋₆ alkoxycarbonylthio C₁₋₆ alkyl, optionally substituted phenylcarbonylthio C₁₋₆ alkyl, optionally substituted phenyl C₁₋₆ alkyl, a group represented by a formula of COR₁, a group represented by a formula of CSR₁, or a group represented by a formula of SO₂R₂; wherein R₁ is C₁₋₁₂ alkyl, C₃₋₆ cycloalkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, optionally substituted phenyl C₁₋₆ alkyl, optionally substituted phenyl C₁₋₆ alkoxy, or optionally substituted phenyl, and R₂ is C₁₋₁₂ alkyl or optionally substituted phenyl; X is nitro, cyano, halogeno, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₁₋₆ haloalkyl, C₂₋₆ aloalkenyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₂₋₆ halkenyloxy, C₂₋₆ haloalkenyloxy, C₂₋₆ alkynyloxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, tri-C₁₋₆ alkylsilyl, C₁₋₆ alkoxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, C₁₋₆ alkylsulfinyl C₁₋₆ alkyl, C₁₋₆ alkylsulfonyl C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkcoxycarbonyl, phenyl C₁₋₆ alkyl optionally substituted by G₂, phenyl C₁₋₆ alkoxy optionally substituted by G₂, thienyl optionally substituted by G₃, pyridyl optionally substituted by G₂, pyridyloxy optionally substituted by G₂, phenyl optionally substituted by G₄, or phenoxy optionally substituted by G₄; wherein G₂ is C₁₋₆ alkyl, halogeno, C₁₋₆ haloalkyl, or C₁₋₆ haloalkoxy, G₃ is C₁₋₆ alkyl or halogeno, and G₄ is nitro cyano, halogeno, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylamino, di-C₁₋₆ alkylamino, C₁₋₆ alkylcarbonyl or C₁₋₆ alkoxycarbonyl; n is 0, or integer of 1 to 5, with the proviso that when A is substituted phenyl, n is not 0, and when n is 2 or more, the above X may be same or different from each other; and Y is oxygen, sulfur, or nitrogen substituted by either hydrogen or C₁₋₆ alkyl, and the salts thereof.
 2. An insecticide or acaricide composition characterized by comprising one or ore of compounds represented by Formula (1);

wherein A, R, X, Y and n are as defined in claim 1 and the salts thereof as the active ingredients. 